Highly Enantioselective Chiral Diol-Catalyzed Conjugate Addition of Boronic Acids to α,β-Unsaturated Trifluoromethyl Ketones

被引：2

作者：

Hou, Ya-Jing ^{[1
]}

Zhao, Lu ^{[1
]}

Chai, Guo-Li ^{[1
]}

Zhong, Kangbao ^{[1
]}

Chang, Junbiao ^{[1
]}

机构：

[1] Henan Normal Univ, Sch Chem & Chem Engn, State Key Lab Antiviral Drugs, Pingyuan Lab, Xinxiang 453007, Henan, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 24期

基金：

中国国家自然科学基金;

关键词：

MEDIATED 1,4-ADDITION REACTION; BOND-FORMING REACTIONS; ALKENYLBORONIC ACIDS; ENONES; ALKYNYLATION; ALKENYLATION; CHEMISTRY; FLUORINE; ARYL;

D O I：

10.1021/acs.joc.3c02281

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The (R)-3,3 '-(3,5-(CF3)(2)-C6H3)(2)-BINOL-catalyzed enantioselective conjugate addition of organic boronic acids to alpha,beta-unsaturated 1,1,1-trifluoromethyl ketones affords corresponding addition products bearing a stereogenic center at the beta-position in moderate to high yields and excellent enantioselectivities (up to 99% ee), without any 1,2-addition product formation. Moreover, this catalytic protocol features mild reaction conditions, a broad substrate scope, suitability for alkenylboronic acids and (hetero)arylboronic acids, and easy scale-up.

引用

页码：17461 / 17471

页数：11

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