{"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. 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. 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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