Stereodivergent Synthesis of Enantioenriched 2,3-Disubstituted Dihydrobenzofurans via a One-Pot C-H Functionalization/Oxa-Michael Addition Cascade

被引：92

作者：

Zhu, Dong-Xing ^{[1
]}

Liu, Jian-Guo ^{[2
,3
]}

Xu, Ming-Hua ^{[2
,3
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China

[2] Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China

[3] Southern Univ Sci & Technol, Dept Chem, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2021年 / 143卷 / 23期

基金：

中国国家自然科学基金;

关键词：

ALPHA-ALLYLATION; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; DUAL CATALYSIS; INSERTION; ORGANOCATALYSIS;

D O I：

10.1021/jacs.1c03498

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A one-pot rhodium-catalyzed C-H functionalization/organocatalyzed oxa-Michael addition cascade reaction has been developed. This methodology enables the stereodivergent synthesis of diverse 2,3-disubstituted dihydrobenzofurans with broad functional group compatibility in good yields with high levels of stereoselectivity under exceptionally mild conditions. The full complement of stereoisomers of chiral 2,3-disubstituted dihydrobenzofurans and 3,4-disubstituted isochromans could be accessed at will by appropriate permutations of the two chiral catalysts. The current work provides a rare example of two chiral catalysts independently controlling two contiguous stereogenic centers subsequently via a two-step reaction in a single operation.

引用

页码：8583 / 8589

页数：7

共 101 条

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