Enantioselective 1,4-addition of diarylphosphine oxides to α,β-unsaturated ketones catalyzed by oxazaborolidines

被引：6

作者：

Qian, Jinyi ^{[2
]}

Zhao, Hengyuan ^{[1
]}

Gao, Qi ^{[2
]}

Chen, Lirong ^{[2
]}

Shi, Yinrui ^{[2
]}

Li, Jiuling ^{[1
]}

Guo, Yafei ^{[1
]}

Fan, Baomin ^{[1
]}

机构：

[1] Yunnan Minzu Univ, Key Lab Adv Synthet Chem Yunnan Minzu Univ State, Sch Chem Environm, Kunming, Yunnan, Peoples R China

[2] Yunnan Minzu Univ, Key Lab Chem Ethn Med Resources, State Ethn Affairs Commiss Minist Educ, Kunming, Yunnan, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 22期

基金：

中国国家自然科学基金;

关键词：

DIELS-ALDER REACTIONS; ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; DIPHENYL PHOSPHITE; MICHAEL ADDITION; CONJUGATE ADDITION; AROMATIC KETONES; REDUCTION; ENONES; (S)-(-)-2-AMINO-3-METHYL-1,1-DIPHENYLBUTAN-1-OL; HYDROPHOSPHINATION;

D O I：

10.1039/d3qo01178j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Classical proline-derived oxazaborolidines as powerful and versatile organocatalysts (CBS, Corey-Bakshi-Shibata) have significant applications in asymmetric catalysis, especially in enantioselective reduction of prochiral ketones and various asymmetric cycloaddition reactions. Despite having been well-studied, their new applications are still very attractive and challenging. Hence, in this research, we disclose a new strategy for the asymmetric carbon-phosphorus bond forming reaction by using CBS catalysts via non-covalent interactions. Notably, various alpha,beta-unsaturated ketones as substrates showed remarkable tolerance to various diarylphosphine oxides. A new application of oxazaborolidines in enantioselective phospha-Michael addition to alpha,beta-unsaturated ketones under mild reaction conditions was developed and the possible mechanism is described.

引用

页码：5672 / 5679

页数：8

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