Stereoselective N-Heterocyclic-Carbene-Catalyzed Formal [4+2] Cycloaddition: Access to Chiral Heterocyclic Cyclohexenones

被引：7
|
作者：
Loska, Ladislav [1 ]
Docekal, Vojtech [1 ]
Cisarova, Ivana [1 ]
Vesely, Jan [1 ]
机构：
[1] Charles Univ Prague, Dept Organ Chem, Fac Sci, Prague 12800 2, Czech Republic
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 01期
关键词：
ENALS; 3-ALKYLENYLOXINDOLES; CONSTRUCTION; DERIVATIVES; CYCLIZATION; ACTIVATION; FUNGUS;
D O I：
10.1021/acs.orglett.2c04021
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The present study reports an asymmetric NHC-catalyzed formal [4 + 2] cycloaddition of heterocyclic alkenes containing a polarized double bond with an azolium-dienolate intermediate generated from alpha-bromo-alpha,beta-unsaturated aldehydes without external oxidation of the Breslow intermediate. Heterocyclic cyclohexenones were produced in good isolated yields (typically about 90%) with good stereochemical outcomes (in most cases, dr > 20/1, and ee = 70-99%). The synthetic utility of the protocol was exemplified by the scope of heterocyclic alkenes.
引用
收藏
页码：174 / 178
页数：5
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