Correction to “P-Stereogenic Phosphorus Ligands in Asymmetric Catalysis”

IF 51.4 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY Chemical Reviews Pub Date : 2024-10-18 DOI:10.1021/acs.chemrev.4c00658
Tsuneo Imamoto
{"title":"Correction to “P-Stereogenic Phosphorus Ligands in Asymmetric Catalysis”","authors":"Tsuneo Imamoto","doi":"10.1021/acs.chemrev.4c00658","DOIUrl":null,"url":null,"abstract":"The original version of this review article contained a number of mistakes including the overlooking of some important achievements and references. The author wishes to correct the mistakes, and sincerely apologizes to the readers and reference authors for any confusion and inconvenience. The following four P-stereogenic phosphorus ligands, <b>LA1</b>,<sup>A</sup> (1)<sup>−A</sup> (3) OXPAMP,<sup>A</sup> (4)<sup>,A</sup> (5)<sup>,351</sup> QUIPHOS,<sup>A</sup> (6)<sup>−A</sup> (9) and <i>t</i>-OctBisP*,<sup>A</sup> (10) should be added in Figure 3. There are errors in the description regarding <b>L26</b> in Figure 3, and they are corrected as shown below. Owing to these additions and corrections, Figure 3 should be replaced by the figure below. Figure 3. P-Stereogenic phosphorus ligands from 1968 to 2000. The numbers in brackets are the enantiomeric excesses of the products obtained in catalytic asymmetric reactions with the ligands: (a) Rh-catalyzed hydrogenation of functionalized alkenes, mostly α-dehydroamino acid derivatives; (b) Pd-catalyzed cross-coupling of 1-phenylethylmagnesium chloride and β-bromostyrene; (c) Pd-catalyzed allylic substitution reaction; (d) Rh-catalyzed hydrosilylation of simple ketones; (e) Kinetic resolution of racemic secondary alcohols by enantioselective acylation; (f) Rh-catalyzed hydroformylation of styrenes; (g) Ni-catalyzed cycloisomerization of 1,6-dienes; (h) Cu-catalyzed Diels−Alder reaction of 3-acryloyl-1,3-oxazolidine-2-one with cyclopentadiene. The following two <i>C</i><sub>2</sub>-symmetric P-stereogenic phosphorus ligands, BeePHOS<sup>227</sup> and JDayPhose,<sup>A</sup> (11) should be added in Figure 5.<img alt=\"\" src=\"/cms/10.1021/acs.chemrev.4c00658/asset/images/medium/cr4c00658_0015.gif\"/> The corrected Figure 5 is provided below. Figure 5. <i>C</i><sub>2</sub>-Symmetric P-stereogenic bisphosphorus ligands and analogous polydentate ligands reported from 2001 to 2023. Page 8664, ligand <b>L81</b> in Figure 6: 2-<i>i</i>-PrC<sub>6</sub>H<sub>4</sub> and 2-<i>t</i>-BuC<sub>6</sub>H<sub>4</sub> are typographical errors for 2-<i>i</i>-PrOC<sub>6</sub>H<sub>4</sub> and 2-<i>t</i>-BuOC<sub>6</sub>H<sub>4</sub>, and they are corrected, as shown below.<img alt=\"\" src=\"/cms/10.1021/acs.chemrev.4c00658/asset/images/medium/cr4c00658_0004.gif\"/> Pages 8669 and 8675, in Tables 1 and 2: The Rh-catalyzed asymmetric hydrogenations of methyl (<i>Z</i>)-α-acetylaminocinnamate (MAC) and (<i>Z</i>)-α-acetylaminocinnamic acid with the use of <i>t</i>-Oct-BisP*, BeePHOS, and JDayPhos are added in Table 1. Some typographical errors in Table 1 are also corrected. The results of the Rh-catalyzed asymmetric hydrogenations of representative β-dehydroamino acid esters with <b>L44</b> and JDayPhos are added in Table 2, along with the correction of some typographical errors. The corrected Tables 1 and 2 are provided here. An A preceding a reference number refers to a reference in this Addition and Correction. This author failed to describe very important achievements that were reported by Stephan, Mohar, and co-workers.<sup>184,219,A</sup> (11)<sup>,A</sup> (12) Page 8679: Scheme A1 should be located before Scheme 32.<sup>184,A</sup> (12) Page 8679: Scheme A2 should be added after Scheme 34.<sup>A</sup> (11) Page 8679: Scheme A3 should be added after Scheme 36.<sup>219</sup> Page 8693, Scheme 109: There are errors in the structure in Scheme 109. The corrected Scheme is provided here. Page 8716, right side: Scheme 232 should be replaced by the following: Other additions and corrections are as follows: Page 8660, left side, line 24, reference numbers: “33−39,74−110” should be replaced by “33−39,74−110,243,351,<sup>A</sup> (1−A10)” (an A preceding a reference number refers to a reference in this Addition and Correction). Page 8663, right side, line 27, references 183,184,219: The following reference should be added: <contrib-group person-group-type=\"allauthors\"><span>Stephan, M.</span>; <span>Sterk, D.</span>; <span>Zupancic, B.</span>; <span>Mohar, B.</span></contrib-group> Profiling the tunable R-SMS-Phos structure in the rhodium(I)-catalyzed hydrogenation of olefins: the last stand?. <cite><i>Org. Biomol. Chem.</i></cite> <span>2011</span>, <em>9</em>, 5266−5271. Page 8670, left side, line 7, reference numbers: “71,319−328” should be replaced by “50,69,71,319−328”. Page 8674, left side, line 5 from the bottom, reference numbers: “42,44,169,184,186,189,202,229,235−238,252,374−376” should be replaced by “42,44,169,180,184,186,189,202,219,229,235−238,252,374−376”. Page 8679, in Scheme 33: “(<i>S</i>)-BulkyP*” should be replaced by “(<i>R</i>)-BulkyP*”. Page 8680, in Scheme 41: “(bnd)” should be replaced by “(nbd)”. Page 8683, left side, line 1: “Rh/Binapine” should be replaced by “Rh/TangPhos”. Page 8685, right side, in Scheme 66: “51% yield from <b>103</b>” should be replaced by “51% yield from <b>104</b>”. Page 8686, right side, in Scheme 72: “MeO” should be replaced by “MeOCH<sub>2</sub>”. Page 8704: There is a typographical error in the title of Scheme 174. “(<b>145</b>)” should be replaced by “(<b>154</b>)”. Page 8708, right side, line 3: “BIBOPO” should be replaced by “BIBOP”. Page 8712, right side, line 1 from the bottom: “48% yield” should be replaced by “46% yield”. Page 8714, right side, line 7, references 661−666: The following reference should be added: <contrib-group person-group-type=\"allauthors\"><span>Ni, H.</span>; <span>Chan, W.-L.</span>; <span>Lu, Y.</span></contrib-group> Phosphine-Catalyzed Asymmetric Reactions. <cite><i>Chem. Rev.</i></cite> <span>2018</span>, <em>118</em>, 9344−9411. This article references 12 other publications. This article has not yet been cited by other publications.","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":"83 1","pages":""},"PeriodicalIF":51.4000,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical Reviews","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.chemrev.4c00658","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0

Abstract

The original version of this review article contained a number of mistakes including the overlooking of some important achievements and references. The author wishes to correct the mistakes, and sincerely apologizes to the readers and reference authors for any confusion and inconvenience. The following four P-stereogenic phosphorus ligands, LA1,A (1)−A (3) OXPAMP,A (4),A (5),351 QUIPHOS,A (6)−A (9) and t-OctBisP*,A (10) should be added in Figure 3. There are errors in the description regarding L26 in Figure 3, and they are corrected as shown below. Owing to these additions and corrections, Figure 3 should be replaced by the figure below. Figure 3. P-Stereogenic phosphorus ligands from 1968 to 2000. The numbers in brackets are the enantiomeric excesses of the products obtained in catalytic asymmetric reactions with the ligands: (a) Rh-catalyzed hydrogenation of functionalized alkenes, mostly α-dehydroamino acid derivatives; (b) Pd-catalyzed cross-coupling of 1-phenylethylmagnesium chloride and β-bromostyrene; (c) Pd-catalyzed allylic substitution reaction; (d) Rh-catalyzed hydrosilylation of simple ketones; (e) Kinetic resolution of racemic secondary alcohols by enantioselective acylation; (f) Rh-catalyzed hydroformylation of styrenes; (g) Ni-catalyzed cycloisomerization of 1,6-dienes; (h) Cu-catalyzed Diels−Alder reaction of 3-acryloyl-1,3-oxazolidine-2-one with cyclopentadiene. The following two C2-symmetric P-stereogenic phosphorus ligands, BeePHOS227 and JDayPhose,A (11) should be added in Figure 5.Abstract Image The corrected Figure 5 is provided below. Figure 5. C2-Symmetric P-stereogenic bisphosphorus ligands and analogous polydentate ligands reported from 2001 to 2023. Page 8664, ligand L81 in Figure 6: 2-i-PrC6H4 and 2-t-BuC6H4 are typographical errors for 2-i-PrOC6H4 and 2-t-BuOC6H4, and they are corrected, as shown below.Abstract Image Pages 8669 and 8675, in Tables 1 and 2: The Rh-catalyzed asymmetric hydrogenations of methyl (Z)-α-acetylaminocinnamate (MAC) and (Z)-α-acetylaminocinnamic acid with the use of t-Oct-BisP*, BeePHOS, and JDayPhos are added in Table 1. Some typographical errors in Table 1 are also corrected. The results of the Rh-catalyzed asymmetric hydrogenations of representative β-dehydroamino acid esters with L44 and JDayPhos are added in Table 2, along with the correction of some typographical errors. The corrected Tables 1 and 2 are provided here. An A preceding a reference number refers to a reference in this Addition and Correction. This author failed to describe very important achievements that were reported by Stephan, Mohar, and co-workers.184,219,A (11),A (12) Page 8679: Scheme A1 should be located before Scheme 32.184,A (12) Page 8679: Scheme A2 should be added after Scheme 34.A (11) Page 8679: Scheme A3 should be added after Scheme 36.219 Page 8693, Scheme 109: There are errors in the structure in Scheme 109. The corrected Scheme is provided here. Page 8716, right side: Scheme 232 should be replaced by the following: Other additions and corrections are as follows: Page 8660, left side, line 24, reference numbers: “33−39,74−110” should be replaced by “33−39,74−110,243,351,A (1−A10)” (an A preceding a reference number refers to a reference in this Addition and Correction). Page 8663, right side, line 27, references 183,184,219: The following reference should be added: Stephan, M.; Sterk, D.; Zupancic, B.; Mohar, B. Profiling the tunable R-SMS-Phos structure in the rhodium(I)-catalyzed hydrogenation of olefins: the last stand?. Org. Biomol. Chem. 2011, 9, 5266−5271. Page 8670, left side, line 7, reference numbers: “71,319−328” should be replaced by “50,69,71,319−328”. Page 8674, left side, line 5 from the bottom, reference numbers: “42,44,169,184,186,189,202,229,235−238,252,374−376” should be replaced by “42,44,169,180,184,186,189,202,219,229,235−238,252,374−376”. Page 8679, in Scheme 33: “(S)-BulkyP*” should be replaced by “(R)-BulkyP*”. Page 8680, in Scheme 41: “(bnd)” should be replaced by “(nbd)”. Page 8683, left side, line 1: “Rh/Binapine” should be replaced by “Rh/TangPhos”. Page 8685, right side, in Scheme 66: “51% yield from 103” should be replaced by “51% yield from 104”. Page 8686, right side, in Scheme 72: “MeO” should be replaced by “MeOCH2”. Page 8704: There is a typographical error in the title of Scheme 174. “(145)” should be replaced by “(154)”. Page 8708, right side, line 3: “BIBOPO” should be replaced by “BIBOP”. Page 8712, right side, line 1 from the bottom: “48% yield” should be replaced by “46% yield”. Page 8714, right side, line 7, references 661−666: The following reference should be added: Ni, H.; Chan, W.-L.; Lu, Y. Phosphine-Catalyzed Asymmetric Reactions. Chem. Rev. 2018, 118, 9344−9411. This article references 12 other publications. This article has not yet been cited by other publications.

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对 "不对称催化中的 P-Stereogenic 磷配体 "的更正
这篇综述文章的原始版本存在一些错误,包括忽略了一些重要成果和参考文献。作者希望纠正这些错误,并对给读者和参考文献作者造成的困惑和不便表示诚挚的歉意。图 3 中应添加以下四种致稳磷配体:LA1,A (1)-A (3) OXPAMP,A (4)-A (5)、351 QUIPHOS,A (6)-A (9) 和 t-OctBisP*,A (10)。图 3 中关于 L26 的描述有误,现更正如下。由于这些补充和更正,图 3 应由下图取代。图 3.1968 年至 2000 年的 P-Stereogenic 磷配体。括号中的数字是与配体进行催化不对称反应所得到产物的对映体过量:(a) Rh 催化的官能化烯氢化反应,主要是 α-脱氢氨基酸衍生物;(b) Pd 催化的 1-苯基乙基氯化镁和 β-溴苯乙烯的交叉偶联反应;(c) Pd 催化的烯丙基取代反应;(d) Rh 催化的简单酮的氢化硅烷化反应;(e) 外消旋仲醇对映体选择性酰化的动力学解析;(f) Rh 催化的苯乙烯氢甲酰化反应;(g) Ni 催化的 1,6 二烯环异构化反应;(h) Cu 催化的 3-丙烯酰基-1,3-恶唑烷-2-酮与环戊二烯的 Diels-Alder 反应。图 5 中应添加以下两个 C2 对称 P-stereogenic 磷配体 BeePHOS227 和 JDayPhose,A (11)。更正后的图 5 如下。图 5.2001 年至 2023 年期间报道的 C2 对称 P-stereogenic 双磷配体和类似的多齿配体。第 8664 页,图 6 中的配体 L81:2-i-PrC6H4 和 2-t-BuC6H4 是 2-i-PrOC6H4 和 2-t-BuOC6H4 的排印错误,现更正如下。第 8669 和 8675 页,表 1 和表 2:表 1 中增加了使用 t-Oct-BisP*、BeePHOS 和 JDayPhos 的 (Z)-α- 乙酰氨基肉桂酸甲酯 (MAC) 和 (Z)-α- 乙酰氨基肉桂酸的 Rh 催化不对称氢化反应。表 1 中的一些印刷错误也得到了更正。表 2 中增加了使用 L44 和 JDayPhos 对代表性 β-脱氢氨基酸酯进行 Rh 催化不对称氢化反应的结果,并更正了一些印刷错误。现提供更正后的表 1 和表 2。参考文献编号前的 A 指的是本增补和更正中的参考文献。该作者没有描述 Stephan、Mohar 和合作者报告的非常重要的成果:方案 A1 应位于方案 32 之前:第 8679 页:方案 A2 应添加到方案 34.A (11) 之后:第 8679 页:应在方案 36.219 之后添加方案 A3 第 8693 页,方案 109:方案 109 中的结构有误。此处提供更正后的方案。第 8716 页,右侧:方案 232 应替换为以下内容:其他补充和更正如下:第 8660 页,左侧,第 24 行,参考编号:"33-39,74-110 "应替换为 "33-39,74-110,243,351,A (1-A10)"(参考号前的 A 指本增补和更正中的参考号)。第 8663 页,右侧第 27 行,参考文献 183、184、219:应添加以下参考文献:Stephan,M.;Sterk,D.;Zupancic,B.;Mohar,B. Profiling the tunable R-SMS-Phos structure in the rhodium(I)-catalyzed hydrogenation of olefins:the last stand?Org.Biomol.Chem.2011, 9, 5266-5271.第 8670 页,左侧第 7 行,参考文献编号:"71,319-328 "应改为 "50,69,71,319-328"。第 8674 页,左侧,自下而上第 5 行,参考编号:"42,44,169,184,186,189,202,229,235-238,252,374-376 "应改为 "42,44,169,180,184,186,189,202,219,229,235-238,252,374-376"。第 8679 页,方案 33 中:应将"(S)-BulkyP*"替换为"(R)-BulkyP*"。第 8680 页,方案 41 中:"(bnd) "应改为"(nbd)"。第 8683 页,左侧第 1 行:"Rh/Binapine "应改为 "Rh/TangPhos"。第 8685 页,右侧,方案 66 中:第 8685 页,右侧,方案 66 中:"103 产率 51%"应改为 "104 产率 51%"。第 8686 页,右侧,方案 72 中:"MeO "应改为 "MeOCH2"。第 8704 页:方案 174 的标题中有一处印刷错误。应将"(145) "改为"(154)"。第 8708 页,右侧第 3 行:"BIBOPO "应改为 "BIBOP"。第 8712 页,右侧,自下而上第 1 行:"48% yield "应改为 "46% yield"。第 8714 页,右侧,第 7 行,参考文献 661-666:应添加以下参考文献:Ni, H.; Chan, W.-L.; Lu, Y. Phosphine-Catalyzed Asymmetric Reactions.Chem.Rev. 2018, 118, 9344-9411。本文引用了 12 篇其他出版物。本文尚未被其他出版物引用。
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来源期刊
Chemical Reviews
Chemical Reviews 化学-化学综合
CiteScore
106.00
自引率
1.10%
发文量
278
审稿时长
4.3 months
期刊介绍: Chemical Reviews is a highly regarded and highest-ranked journal covering the general topic of chemistry. Its mission is to provide comprehensive, authoritative, critical, and readable reviews of important recent research in organic, inorganic, physical, analytical, theoretical, and biological chemistry. Since 1985, Chemical Reviews has also published periodic thematic issues that focus on a single theme or direction of emerging research.
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