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

页码：174 / 178

页数：5

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