A Highly Enantioselective Homoenolate Michael Addition/Esterification Sequence of Cyclohexadienone-Tethered Enals via NHC Catalysis

被引：16
|
作者：
Wang, Ya-Jie [1 ]
Wang, Yi-Fan [1 ]
Kang, Wen-Yu [1 ]
Lu, Wen-Ya [1 ]
Wang, Yu-Hui [1 ]
Tian, Ping [1 ]
机构：
[1] Shanghai Univ Tradit Chinese Med, Innovat Res Inst Tradit Chinese Med, Res Ctr Chiral Drugs, Shanghai Frontiers Sci Ctr TCM Chem Biol, Shanghai 201203, Peoples R China
来源：
ORGANIC LETTERS | 2023年
基金：
中国国家自然科学基金; 国家重点研发计划;
关键词：
GAMMA-BUTYROLACTONES; CONJUGATE UMPOLUNG; CONSTRUCTION;
D O I：
10.1021/acs.orglett.2c04183
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reported here is a highly enantioselective homoenolate Michael addition/esterification sequence of cyclo-hexadienone-tethered enals via N-heterocyclic carbene (NHC) catalysis, affording the enantiopure cis-hydrobenzofurans, cis-hydroindoles, and cis-hydroindenes. The NHC catalyst bearing a nitro group greatly enhances the stereocontrol, and a bulky N-aryl substituent of the triazolium salt in the catalyst is helpful for inhibiting the further aldol condensation after homoenolate Michael addition. The utility of this protocol is highlighted by a gram-scale experiment and versatile downstream transformations.
引用
收藏
页码：630 / 635
页数：6
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