Asymmetric Bromoaminocyclization and Desymmetrization of Cyclohexa-1,4-dienes through Anion Phase-Transfer Catalysis

被引：18

作者：

Long, Hai-Jiao ^{[1
]}

Li, Yin-Long ^{[1
]}

Zhang, Bing-Qian ^{[1
]}

Xiao, Wen-Ying ^{[1
]}

Zhang, Xiao-Ying ^{[1
]}

He, Ling ^{[1
]}

Deng, Jun ^{[1
]}

机构：

[1] Chongqing Univ, Sch Pharmaceut Sci, Chongqing Key Lab Nat Prod Synth & Drug Res, Chongqing 401331, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 21期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE BROMOAMINOCYCLIZATION; ALKENES; BROMOCYCLIZATION; HALOFUNCTIONALIZATION; TOSYLCARBAMATES; HALOGENATION; STRATEGY;

D O I：

10.1021/acs.orglett.1c02817

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic enantioselective desymmetrizing bromoaminocyclization of prochiral cyclohexa-1,4-dienes has been achieved by using chiral anion phase-transfer catalysis, providing a range of enantioenriched cis-3a-arylhydroindoles bearing an all-carbon quaternary stereocenter in good yields (up to 78%) and excellent enantioselectivities (up to 97% ee). Furthermore, the potential application of this methodology to natural product total synthesis was demonstrated by the asymmetric synthesis of (+)-Mesembrane.

引用

页码：8153 / 8157

页数：5

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