Pub Date : 2025-09-15DOI: 10.1016/j.tetlet.2025.155827
Anastasia Charlery, Shrey P. Desai, Matthew T. Zambri, Mark S. Taylor
In the presence of the sugar alcohol meso-erythritol, trans-2-arylvinylboronic acids undergo regio- and diastereoselective, photocatalytic [2 + 2] cycloadditions, generating all-trans-substituted cyclobutane-1,2-bis(boronic acid) derivatives. A covalent templating mechanism is proposed, involving in situ formation of a 2:1 boronic acid:tetraol adduct – likely a mixed boronic ester/hemiboronic ester. The protocol has been applied to various substituted trans-2-arylvinylboronic acid derivatives, providing access to chiral, C2-symmetric cyclobutane derivatives that would be challenging to synthesize by other means.
{"title":"Diastereoselective, photocatalytic [2 + 2] dimerizations of alkenylboronic acids promoted by sugar alcohols","authors":"Anastasia Charlery, Shrey P. Desai, Matthew T. Zambri, Mark S. Taylor","doi":"10.1016/j.tetlet.2025.155827","DOIUrl":"10.1016/j.tetlet.2025.155827","url":null,"abstract":"<div><div>In the presence of the sugar alcohol <em>meso</em>-erythritol, <em>trans-</em>2-arylvinylboronic acids undergo regio- and diastereoselective, photocatalytic [2 + 2] cycloadditions, generating all-<em>trans</em>-substituted cyclobutane-1,2-bis(boronic acid) derivatives. A covalent templating mechanism is proposed, involving in situ formation of a 2:1 boronic acid:tetraol adduct – likely a mixed boronic ester/hemiboronic ester. The protocol has been applied to various substituted <em>trans</em>-2-arylvinylboronic acid derivatives, providing access to chiral, C2-symmetric cyclobutane derivatives that would be challenging to synthesize by other means.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155827"},"PeriodicalIF":1.5,"publicationDate":"2025-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145109543","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The stereoselective Baeyer–Villiger oxidation of 3-arylcyclobutanones was achieved using a flavinium-based ion-pair catalyst system. Systematic variation of catalyst and substrate structures revealed key structure–selectivity relationships. A simplified catalyst bearing a single stereocenter demonstrated improved or comparable enantioselectivity relative to the original catalyst. Substrates bearing substituents capable of hydrogen–bond donor substituents on the aromatic ring showed enhanced enantioselectivity, with the optimal catalyst–substrate combination affording the γ-lactone product in up to 99% ee.
{"title":"Structure–selectivity correlation in asymmetric baeyer–villiger oxidation of 3-arylcyclobutanones by a flavinium ion-pair catalyst","authors":"Junya Fujimoto , Eika Suruga , Natsuhiko Sugimura , Kana Yamamoto","doi":"10.1016/j.tetlet.2025.155826","DOIUrl":"10.1016/j.tetlet.2025.155826","url":null,"abstract":"<div><div>The stereoselective Baeyer–Villiger oxidation of 3-arylcyclobutanones was achieved using a flavinium-based ion-pair catalyst system. Systematic variation of catalyst and substrate structures revealed key structure–selectivity relationships. A simplified catalyst bearing a single stereocenter demonstrated improved or comparable enantioselectivity relative to the original catalyst. Substrates bearing substituents capable of hydrogen–bond donor substituents on the aromatic ring showed enhanced enantioselectivity, with the optimal catalyst–substrate combination affording the γ-lactone product in up to 99% ee.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155826"},"PeriodicalIF":1.5,"publicationDate":"2025-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145105226","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-09-13DOI: 10.1016/j.tetlet.2025.155758
Hiroki Miura , Miyu Chida , Tetsuya Shishido
Supported Au catalysts efficiently promoted the borylation of C(sp2)–H bonds in indoles. The reaction proceeded with high regioselectivity at the C3 position, affording C3-borylated indoles in good to excellent yields. Notably, the supported Au catalysts demonstrated reusability over multiple cycles, and the reaction was readily scalable to the gram scale without loss of efficiency. Mechanistic studies suggest that the borylation proceeds via the formation of radical intermediates, generated by single electron transfer catalysis of Au nanoparticles.
{"title":"C3-selective CH borylation of indoles by supported gold catalysts","authors":"Hiroki Miura , Miyu Chida , Tetsuya Shishido","doi":"10.1016/j.tetlet.2025.155758","DOIUrl":"10.1016/j.tetlet.2025.155758","url":null,"abstract":"<div><div>Supported Au catalysts efficiently promoted the borylation of C(sp<sup>2</sup>)–H bonds in indoles. The reaction proceeded with high regioselectivity at the C3 position, affording C3-borylated indoles in good to excellent yields. Notably, the supported Au catalysts demonstrated reusability over multiple cycles, and the reaction was readily scalable to the gram scale without loss of efficiency. Mechanistic studies suggest that the borylation proceeds via the formation of radical intermediates, generated by single electron transfer catalysis of Au nanoparticles.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155758"},"PeriodicalIF":1.5,"publicationDate":"2025-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145105145","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-09-12DOI: 10.1016/j.tetlet.2025.155819
Chang Liu, Qiping He, Haiyue Yang, Hao Jin, Siyu Wang, Mingquan Yuan, Yi Jin
Herein we report a regioselective oxidative C(sp2)–H thiocyanation/selenocyanation of arylamines using commercially available and inexpensive NaSCN/KSeCN as sulfur/selenium sources. This method employs a non-transition bismuth catalyst under visible-light irradiation, operating through a photoinduced ligand-to-metal charge transfer (LMCT) homolysis mechanism. The transient BiN complex, formed via coordination of the arylamine nitrogen to bismuth, undergoes LMCT-triggered homolytic BiN bond cleavage upon irradiation. This generates a nitrogen-centered radical intermediate that isomerizes to a para-aryl radical via regioselective intramolecular hydrogen atom transfer (HAT). Subsequent radical cross-coupling with thiocyanate/selenocyanate nucleophiles forges CS or CSe bonds with exclusive para-selectivity. The protocol features mild conditions, broad functional group tolerance, and avoids stoichiometric oxidants.
{"title":"Photoinduced regioselective CH thiocyanation and selenocyanation of arylamines","authors":"Chang Liu, Qiping He, Haiyue Yang, Hao Jin, Siyu Wang, Mingquan Yuan, Yi Jin","doi":"10.1016/j.tetlet.2025.155819","DOIUrl":"10.1016/j.tetlet.2025.155819","url":null,"abstract":"<div><div>Herein we report a regioselective oxidative C(sp<sup>2</sup>)–H thiocyanation/selenocyanation of arylamines using commercially available and inexpensive NaSCN/KSeCN as sulfur/selenium sources. This method employs a non-transition bismuth catalyst under visible-light irradiation, operating through a photoinduced ligand-to-metal charge transfer (LMCT) homolysis mechanism. The transient Bi<img>N complex, formed via coordination of the arylamine nitrogen to bismuth, undergoes LMCT-triggered homolytic Bi<img>N bond cleavage upon irradiation. This generates a nitrogen-centered radical intermediate that isomerizes to a <em>para</em>-aryl radical via regioselective intramolecular hydrogen atom transfer (HAT). Subsequent radical cross-coupling with thiocyanate/selenocyanate nucleophiles forges C<img>S or C<img>Se bonds with exclusive <em>para</em>-selectivity. The protocol features mild conditions, broad functional group tolerance, and avoids stoichiometric oxidants.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155819"},"PeriodicalIF":1.5,"publicationDate":"2025-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145105144","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-09-11DOI: 10.1016/j.tetlet.2025.155822
Satsuki Fukui , Itsuku Makigawa , Yuya Machi , Hideo Kojima , Satomi Takeda , Rio Yamanaka
The asymmetric reduction of fluorinated ketones (1a–c) was investigated using the wild-type cyanobacterium Synechocystis sp. PCC 6803 at 25 °C for 24 h. Under red LED illumination (660 nm, 10 μmol m−2 s−1), the photosynthetic system promoted cofactor regeneration, enhancing the formation of optically active alcohols (2a–c). The effect of substrate concentration was found to significantly influence stereoselectivity: at low concentrations, L-alcohols were predominantly formed, whereas at higher concentrations, a shift toward D-selectivity was observed, especially for substrate 1c (41 % ee (L) at 0.05 mM; 87 % ee (D) at 5 mM). Furthermore, 1a acted as a competitive inhibitor in the reduction of 1c, effectively altering the enantioselectivity. Additionally, hyperosmotic conditions induced by 0.5 M sorbitol or 0.25 M NaCl increased the yield of L-alcohols, likely by upregulating the expression of the fabG gene, which encodes an NADPH-dependent ketoreductase. These findings provide new insights into the control of stereoselectivity and reaction efficiency in photobiocatalytic reductions using whole-cell cyanobacteria.
利用野生型蓝细菌Synechocystis sp. PCC 6803，在25°C、24 h下研究了氟化酮（1a-c）的不对称还原。在红色LED照明（660 nm、10 μmol m−2 s−1）下，光合系统促进了辅因子的再生，促进了光学活性醇（2a-c）的形成。发现底物浓度的影响显著影响立体选择性：在低浓度下，主要形成L-醇，而在较高浓度下，观察到向d -选择性的转变，特别是底物1c (41% ee (L), 0.05 mM；87% ee (D)在5毫米)。此外，1a在1c的还原中起到竞争性抑制剂的作用，有效地改变了对映体的选择性。此外，0.5 M山梨醇或0.25 M NaCl诱导的高渗条件增加了l -醇的产量，可能是通过上调编码nadph依赖性酮还原酶的fabG基因的表达。这些发现为利用全细胞蓝藻控制光催化还原中的立体选择性和反应效率提供了新的见解。
{"title":"Effect of additives on the asymmetric reduction of fluorinated ketones using cyanobacterium Synechocystis sp. PCC 6803","authors":"Satsuki Fukui , Itsuku Makigawa , Yuya Machi , Hideo Kojima , Satomi Takeda , Rio Yamanaka","doi":"10.1016/j.tetlet.2025.155822","DOIUrl":"10.1016/j.tetlet.2025.155822","url":null,"abstract":"<div><div>The asymmetric reduction of fluorinated ketones (<strong>1a–c</strong>) was investigated using the wild-type cyanobacterium Synechocystis sp. PCC 6803 at 25 °C for 24 h. Under red LED illumination (660 nm, 10 μmol m<sup>−2</sup> s<sup>−1</sup>), the photosynthetic system promoted cofactor regeneration, enhancing the formation of optically active alcohols (<strong>2a–c</strong>). The effect of substrate concentration was found to significantly influence stereoselectivity: at low concentrations, L-alcohols were predominantly formed, whereas at higher concentrations, a shift toward D-selectivity was observed, especially for substrate <strong>1c</strong> (41 % ee (L) at 0.05 mM; 87 % ee (D) at 5 mM). Furthermore, <strong>1a</strong> acted as a competitive inhibitor in the reduction of <strong>1c</strong>, effectively altering the enantioselectivity. Additionally, hyperosmotic conditions induced by 0.5 M sorbitol or 0.25 M NaCl increased the yield of L-alcohols, likely by upregulating the expression of the fabG gene, which encodes an NADPH-dependent ketoreductase. These findings provide new insights into the control of stereoselectivity and reaction efficiency in photobiocatalytic reductions using whole-cell cyanobacteria.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155822"},"PeriodicalIF":1.5,"publicationDate":"2025-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145105228","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-09-11DOI: 10.1016/j.tetlet.2025.155825
Phuong T. Dinh , Quan Q.T. Pham , Dat T. Huynh , Tung T. Nguyen , Ngoc D.Q. Chau
Synthesis of 3-aminoindole derivatives via a cascade coupling of 2′-nitrochalcones and NH bonds in pyrazoles under the assistance of copper iron oxide is firstly reported. Our approach would provide an alternative to avoid the requirement of strong base and/or unrecoverable transition metal salt. Characterization of the spent copper iron oxide by XRD, FT-IR, and N2 physisorption revealed that the structure of the material did not change during the reaction. Scope of the substrates was also attempted, confirming the compatiblity of several weakly-nucleophilic pyrazoles.
{"title":"Copper iron oxide promoted cascade annulation between 2′-nitrochalcones and NH pyrazoles","authors":"Phuong T. Dinh , Quan Q.T. Pham , Dat T. Huynh , Tung T. Nguyen , Ngoc D.Q. Chau","doi":"10.1016/j.tetlet.2025.155825","DOIUrl":"10.1016/j.tetlet.2025.155825","url":null,"abstract":"<div><div>Synthesis of 3-aminoindole derivatives via a cascade coupling of 2′-nitrochalcones and N<img>H bonds in pyrazoles under the assistance of copper iron oxide is firstly reported. Our approach would provide an alternative to avoid the requirement of strong base and/or unrecoverable transition metal salt. Characterization of the spent copper iron oxide by XRD, FT-IR, and N<sub>2</sub> physisorption revealed that the structure of the material did not change during the reaction. Scope of the substrates was also attempted, confirming the compatiblity of several weakly-nucleophilic pyrazoles.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155825"},"PeriodicalIF":1.5,"publicationDate":"2025-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145105222","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-09-10DOI: 10.1016/j.tetlet.2025.155823
Mizuki Kadota, King Hung Nigel Tang, Takanori Shibata
This study presents the iridium-catalyzed branch- and enantioselective CH alkylation of acetanilides with internal alkenes via chain-walking. This report addresses a key challenge in the selective CC bond formation by using a newly developed electron-deficient TADDOL-based chiral ligand and we achieved an optimal balance between yield and enantiomeric ratio (up to 91:9 er). The use of 1.5 equivalent amounts of [Ir(cod)2]NTf2 relative to chiral ligands significantly improved the yields along with perfect regioselectivity and good enantioselectivity. The substrate scope demonstrated the broad applicability of the method across various acetanilide and alkene derivatives, including functionalized arenes and alkenes bearing aryl or aliphatic substituents.
{"title":"Ir-catalyzed distal branch- and enantioselective hydroarylation of internal alkenes using acetanilides via chain-walking and CH activation","authors":"Mizuki Kadota, King Hung Nigel Tang, Takanori Shibata","doi":"10.1016/j.tetlet.2025.155823","DOIUrl":"10.1016/j.tetlet.2025.155823","url":null,"abstract":"<div><div>This study presents the iridium-catalyzed branch- and enantioselective C<img>H alkylation of acetanilides with internal alkenes via chain-walking. This report addresses a key challenge in the selective C<img>C bond formation by using a newly developed electron-deficient TADDOL-based chiral ligand and we achieved an optimal balance between yield and enantiomeric ratio (up to 91:9 er). The use of 1.5 equivalent amounts of [Ir(cod)<sub>2</sub>]NTf<sub>2</sub> relative to chiral ligands significantly improved the yields along with perfect regioselectivity and good enantioselectivity. The substrate scope demonstrated the broad applicability of the method across various acetanilide and alkene derivatives, including functionalized arenes and alkenes bearing aryl or aliphatic substituents.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"173 ","pages":"Article 155823"},"PeriodicalIF":1.5,"publicationDate":"2025-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145157010","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-09-07DOI: 10.1016/j.tetlet.2025.155821
Bagrat A. Shainyan , Mark V. Sigalov
In the present review, two types of compounds capable of tautomerization with proton transfer between N and O atoms, isomerization by rotation about the CC or CN bonds, and hydrogen bonding in specific isomers are analyzed, focusing on the last two decades. The first type is enaminones attracting a growing interest as synthetic precursors of heterocycles, or, structurally, as push-pull ethylenes. This reduces the barrier to rotation around the double bond, and increases the barrier to rotation around the adjacent single bond. Another type of compounds also capable of tautomerism, conformational and rotational equilibrium, and the hydrogen bonding, is keto- or diketoenols with aromatic N-heterocycles at the CC bond which have been investigated mainly by our research groups. Overall, the review summarizes recent advances in studying E/Z isomerization, tautomerism, H-bonding in enaminones and ketoenols, and relationship between these phenomena.
{"title":"Tautomerism, Z/E isomerization, and H-bonding in the amino and N-hetaryl derivatives of carbonyl compounds","authors":"Bagrat A. Shainyan , Mark V. Sigalov","doi":"10.1016/j.tetlet.2025.155821","DOIUrl":"10.1016/j.tetlet.2025.155821","url":null,"abstract":"<div><div>In the present review, two types of compounds capable of tautomerization with proton transfer between N and O atoms, isomerization by rotation about the C<img>C or C<img>N bonds, and hydrogen bonding in specific isomers are analyzed, focusing on the last two decades. The first type is enaminones attracting a growing interest as synthetic precursors of heterocycles, or, structurally, as push-pull ethylenes. This reduces the barrier to rotation around the double bond, and increases the barrier to rotation around the adjacent single bond. Another type of compounds also capable of tautomerism, conformational and rotational equilibrium, and the hydrogen bonding, is keto- or diketoenols with aromatic N-heterocycles at the C<img>C bond which have been investigated mainly by our research groups. Overall, the review summarizes recent advances in studying <em>E/Z</em> isomerization, tautomerism, H-bonding in enaminones and ketoenols, and relationship between these phenomena.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155821"},"PeriodicalIF":1.5,"publicationDate":"2025-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145026964","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-09-05DOI: 10.1016/j.tetlet.2025.155820
Kailas Arjun Chavan , Omkar A. Sonawane , Rohan D. Erande
Aiming to find novel natural products along with establishing a simple isolation process, here we described the efficient isolation of pterostilbene along with three unreported compounds – di-pterostilbene; 3,5-dimethoxybenzyl alcohol; and 5,5′-(oxybis(methylene))bis(1,3-dimethoxybenzene) from the heartwood of P. marsupium via a simple silica-gel flash column chromatography. A comprehensive structural elucidation of all the isolated compounds was done using spectroscopic techniques such as 1H NMR, 13C NMR, 13C-DEPT135, 1H–1H COSY, FT-IR and HRMS. Furthermore, in silico molecular docking studies of newly isolated molecules reveal to exhibit strong binding affinities towards antidiabetic and anticancer targets involved in glucose homeostasis, insulin signalling, and tumor progression. Additionally, in vitro cytotoxicity evaluation against A549 lung carcinoma cells revealed antiproliferative activity, which makes them promising therapeutic agents along with emerging lead scaffolds for antidiabetic and anticancer drug development.
{"title":"Novel metabolites from Pterocarpus marsupium: Structural characterization and biological relevance","authors":"Kailas Arjun Chavan , Omkar A. Sonawane , Rohan D. Erande","doi":"10.1016/j.tetlet.2025.155820","DOIUrl":"10.1016/j.tetlet.2025.155820","url":null,"abstract":"<div><div>Aiming to find novel natural products along with establishing a simple isolation process, here we described the efficient isolation of pterostilbene along with three unreported compounds – di-pterostilbene; 3,5-dimethoxybenzyl alcohol; and 5,5′-(oxybis(methylene))bis(1,3-dimethoxybenzene) from the heartwood of <em>P. marsupium via</em> a simple silica-gel flash column chromatography. A comprehensive structural elucidation of all the isolated compounds was done using spectroscopic techniques such as <sup>1</sup>H NMR, <sup>13</sup>C NMR, <sup>13</sup>C-DEPT135, <sup>1</sup>H–<sup>1</sup>H COSY, FT-IR and HRMS. Furthermore, <em>in silico</em> molecular docking studies of newly isolated molecules reveal to exhibit strong binding affinities towards antidiabetic and anticancer targets involved in glucose homeostasis, insulin signalling, and tumor progression. Additionally, <em>in vitro</em> cytotoxicity evaluation against A549 lung carcinoma cells revealed antiproliferative activity, which makes them promising therapeutic agents along with emerging lead scaffolds for antidiabetic and anticancer drug development.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155820"},"PeriodicalIF":1.5,"publicationDate":"2025-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145019782","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-09-04DOI: 10.1016/j.tetlet.2025.155818
Xinxin Yuan , Qianding Zeng , Liyuan Luo , Yuanhao Chen , Jie Gu , Xinyu Zhu , Wenjun Jin , Jiangmeng Ren , Bu-Bing Zeng
Herein, we developed a new method for the deprotection of N-allyloxycarbonyl (Alloc) using a NiCl₂/NaBH₄ system to provide the parent amino compounds with good to excellent yields. Notably, this practical protocol exhibits excellent compatibility with various N-alloc protected amines with different functional groups that derived from multi-substituted anilines, heteroaromatic and aliphatic amines or even some secondary amines. The mechanism of the reaction is also demonstrated.
{"title":"Deprotection of N-Allyloxycarbonyl groups using the NiCl2/NaBH4 system","authors":"Xinxin Yuan , Qianding Zeng , Liyuan Luo , Yuanhao Chen , Jie Gu , Xinyu Zhu , Wenjun Jin , Jiangmeng Ren , Bu-Bing Zeng","doi":"10.1016/j.tetlet.2025.155818","DOIUrl":"10.1016/j.tetlet.2025.155818","url":null,"abstract":"<div><div>Herein, we developed a new method for the deprotection of <em>N</em>-allyloxycarbonyl (Alloc) using a NiCl₂/NaBH₄ system to provide the parent amino compounds with good to excellent yields. Notably, this practical protocol exhibits excellent compatibility with various <em>N</em>-alloc protected amines with different functional groups that derived from multi-substituted anilines, heteroaromatic and aliphatic amines or even some secondary amines. The mechanism of the reaction is also demonstrated.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"171 ","pages":"Article 155818"},"PeriodicalIF":1.5,"publicationDate":"2025-09-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145026850","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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