Conversion of C-terminal carboxy groups of N-protected α-amino acids to the corresponding 3,5-dinitrobenzoyl mixed anhydrides, followed by treatment with α-azido esters and trialkylphosphines, affords good yields of peptides, without appreciable formation of epimers even for reactions involving Phe–Val and Val–Val couplings and/or N-benzoyl α-amino acids.
{"title":"Epimerisation-free peptide formation from carboxylic acid anhydrides and azido derivatives","authors":"I. Bosch, F. Urpí, J. Vilarrasa","doi":"10.1039/C39950000091","DOIUrl":"https://doi.org/10.1039/C39950000091","url":null,"abstract":"Conversion of C-terminal carboxy groups of N-protected α-amino acids to the corresponding 3,5-dinitrobenzoyl mixed anhydrides, followed by treatment with α-azido esters and trialkylphosphines, affords good yields of peptides, without appreciable formation of epimers even for reactions involving Phe–Val and Val–Val couplings and/or N-benzoyl α-amino acids.","PeriodicalId":17282,"journal":{"name":"Journal of The Chemical Society, Chemical Communications","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"1995-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78346438","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
M. Drew, C. Harding, V. McKee, G. G. Morgan, J. Nelson
Comparison of the structures of four monomanganese (and one monoiron) complexes of ligands with the identical donor [N3(O–)3] set reveals that geometry determines the redox state of the cation.
{"title":"Geometric control of manganese redox state","authors":"M. Drew, C. Harding, V. McKee, G. G. Morgan, J. Nelson","doi":"10.1039/C39950001035","DOIUrl":"https://doi.org/10.1039/C39950001035","url":null,"abstract":"Comparison of the structures of four monomanganese (and one monoiron) complexes of ligands with the identical donor [N3(O–)3] set reveals that geometry determines the redox state of the cation.","PeriodicalId":17282,"journal":{"name":"Journal of The Chemical Society, Chemical Communications","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"1995-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78371904","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Diethyl(prop-1-ynyl)borane 1 reacts, in the presence of a large excess of tetraethyldiborane(6), to give the new substituted 1-carba-arachno-pentaborane(10)4 as the first intermediate which can be isolated; 4 rearranges via the nido-C2B4(8) carbaboranes A and Bto the known pentaethyl-1,5-dicarba-closo-pentaborane(5)5which is characterized by single crystal X-ray analysis.
{"title":"Condensation route from 1,1,1-tris(diethylboryl)propane to pentaethyl-1,5-dicarba-closo-pentaborane(5)via arachno-CB4(10) and nido-C2B4(8) carbaboranes","authors":"R. Köster, R. Boese, B. Wrackmeyer, H. Schanz","doi":"10.1039/C39950001691","DOIUrl":"https://doi.org/10.1039/C39950001691","url":null,"abstract":"Diethyl(prop-1-ynyl)borane 1 reacts, in the presence of a large excess of tetraethyldiborane(6), to give the new substituted 1-carba-arachno-pentaborane(10)4 as the first intermediate which can be isolated; 4 rearranges via the nido-C2B4(8) carbaboranes A and Bto the known pentaethyl-1,5-dicarba-closo-pentaborane(5)5which is characterized by single crystal X-ray analysis.","PeriodicalId":17282,"journal":{"name":"Journal of The Chemical Society, Chemical Communications","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"1995-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78511698","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
S. Araneo, F. Fontana, F. Minisci, F. Recupero, A. Serri
New general syntheses, based on free-radical oxidative alkylation, acylation and arylation of acrylonitrile, in the presence of ButO2H, are reported; the concept of the peroxy group as a pseudohalide is suggested to explain these new reactions.
{"title":"Hydroperoxides as pseudohalides: oxidation, oxidative alkylation, acylation and arylation of acrylonitrile","authors":"S. Araneo, F. Fontana, F. Minisci, F. Recupero, A. Serri","doi":"10.1039/C39950001399","DOIUrl":"https://doi.org/10.1039/C39950001399","url":null,"abstract":"New general syntheses, based on free-radical oxidative alkylation, acylation and arylation of acrylonitrile, in the presence of ButO2H, are reported; the concept of the peroxy group as a pseudohalide is suggested to explain these new reactions.","PeriodicalId":17282,"journal":{"name":"Journal of The Chemical Society, Chemical Communications","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"1995-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77429083","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
T. J. Norman, D. Parker, L. Royle, A. Harrison, Pari Antoniwb, David J. Kingb
Linkage of a macrocyclic complexing agent to a spaced tri-maleimide allows formation of a recombinant trivalent antibody by reaction with a Δ-Cys Fab fragment of an engineered human antibody.
{"title":"Improved tumour targeting with recombinant antibody–macrocycle conjugates","authors":"T. J. Norman, D. Parker, L. Royle, A. Harrison, Pari Antoniwb, David J. Kingb","doi":"10.1039/C39950001877","DOIUrl":"https://doi.org/10.1039/C39950001877","url":null,"abstract":"Linkage of a macrocyclic complexing agent to a spaced tri-maleimide allows formation of a recombinant trivalent antibody by reaction with a Δ-Cys Fab fragment of an engineered human antibody.","PeriodicalId":17282,"journal":{"name":"Journal of The Chemical Society, Chemical Communications","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"1995-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"72860046","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The diastereoisomerism of some spiro 1,3-dioxanes with axial chirality and of some trispiro derivatives exhibiting an axial and a hitherto unreported helical chirality for spiranic compounds is discussed.
{"title":"Axial and helical chirality of some spiro-1,3-dioxanes","authors":"I. Grosu, S. Mager, G. Plé, Mihai Horn","doi":"10.1039/C39950000167","DOIUrl":"https://doi.org/10.1039/C39950000167","url":null,"abstract":"The diastereoisomerism of some spiro 1,3-dioxanes with axial chirality and of some trispiro derivatives exhibiting an axial and a hitherto unreported helical chirality for spiranic compounds is discussed.","PeriodicalId":17282,"journal":{"name":"Journal of The Chemical Society, Chemical Communications","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"1995-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"72917864","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
C60 reacts with cyclopent-2-enone ethylene acetal to give C60-fused norbornan-2-one acetal; modification of the starting acetal with a chiral auxiliary leads to a mixture of diastereoisomeric adducts from which a pair of enantiomerically pure C60-fused norbornan-2-ones are readily obtained.
{"title":"Reaction of C60 with cyclopent-2-enone acetals. A convenient access to chiral C60 derivatives","authors":"M. Ohkita, Koh Ishigami, T. Tsuji","doi":"10.1039/C39950001769","DOIUrl":"https://doi.org/10.1039/C39950001769","url":null,"abstract":"C60 reacts with cyclopent-2-enone ethylene acetal to give C60-fused norbornan-2-one acetal; modification of the starting acetal with a chiral auxiliary leads to a mixture of diastereoisomeric adducts from which a pair of enantiomerically pure C60-fused norbornan-2-ones are readily obtained.","PeriodicalId":17282,"journal":{"name":"Journal of The Chemical Society, Chemical Communications","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"1995-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73128193","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
D. Barr, W. Clegg, Lucy Cowton, Lynne Horsburgh, Fiona M. Mackenzie, R. Mulvey
Lithium structural chemistry continues to surprise as highlighted here by the reaction of BunLi, aniline and pmdeta, which by analogy with related systems, should yield a simple monomeric complex, when, in fact, an unprecedented trinuclear formulation is produced; in contrast, the corresponding Na system falls into line with predictions, in yielding a dimeric product.
{"title":"Lithium anilide complexed by pmdeta: expectation of a simple monomer, but in reality an odd trinuclear composition combining three-, four- and five-coordinate lithium","authors":"D. Barr, W. Clegg, Lucy Cowton, Lynne Horsburgh, Fiona M. Mackenzie, R. Mulvey","doi":"10.1039/C39950000891","DOIUrl":"https://doi.org/10.1039/C39950000891","url":null,"abstract":"Lithium structural chemistry continues to surprise as highlighted here by the reaction of BunLi, aniline and pmdeta, which by analogy with related systems, should yield a simple monomeric complex, when, in fact, an unprecedented trinuclear formulation is produced; in contrast, the corresponding Na system falls into line with predictions, in yielding a dimeric product.","PeriodicalId":17282,"journal":{"name":"Journal of The Chemical Society, Chemical Communications","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"1995-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73417055","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
P. Magnus, L. Diorazio, T. Donohoe, M. Giles, P. Pye, James G. Tarrant, S. Thom
Solvolysis of the neopentyl triflates 14, 25 and 32 resulted in ring expansion of a seven-membered ring into the eight-membered ring required for the synthesis of the taxanes diterpenoids.
新戊基三氟酸酯14,25和32的溶剂溶解导致七元环扩展为合成紫杉烷二萜所需的八元环。
{"title":"New strategy for the synthesis of the taxane diterpenes: formation of the eight-membered B-ring of taxol by semi-pinacol rearrangement","authors":"P. Magnus, L. Diorazio, T. Donohoe, M. Giles, P. Pye, James G. Tarrant, S. Thom","doi":"10.1039/C39950001935","DOIUrl":"https://doi.org/10.1039/C39950001935","url":null,"abstract":"Solvolysis of the neopentyl triflates 14, 25 and 32 resulted in ring expansion of a seven-membered ring into the eight-membered ring required for the synthesis of the taxanes diterpenoids.","PeriodicalId":17282,"journal":{"name":"Journal of The Chemical Society, Chemical Communications","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"1995-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73417331","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
G. Delogu, D. Fabbri, F. Fabris, F. Sbrogiò, G. Valle, O. Lucchi
Singlet oxygen undergoes cycloaddition to bisdialine 1 to afford predominantly the anti adduct 2, while the expected syn product 3 is formed only in low yield.
单线态氧与双双苯胺1发生环加成反应，主要生成抗加合物2，而预期的合成产物3产率较低。
{"title":"SYN AND ANTI CYCLOADDITION OF SINGLET OXYGEN TO BISDIALINE","authors":"G. Delogu, D. Fabbri, F. Fabris, F. Sbrogiò, G. Valle, O. Lucchi","doi":"10.1039/C39950001887","DOIUrl":"https://doi.org/10.1039/C39950001887","url":null,"abstract":"Singlet oxygen undergoes cycloaddition to bisdialine 1 to afford predominantly the anti adduct 2, while the expected syn product 3 is formed only in low yield.","PeriodicalId":17282,"journal":{"name":"Journal of The Chemical Society, Chemical Communications","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"1995-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79900835","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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