Enantioselective Cascade Annulation of alpha-Amino-ynones and Enals Enabled by Gold and Oxidative NHC Relay Catalysis
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION(2022)
摘要
We report herein an unprecedented gold and oxidative NHC relay catalysis that enables highly enantioselective cascade annulation between readily available alpha-amino-ynones with enals. This method utilizes the in situ-generated pyrrolin-4-ones as a novel and versatile synthon, which engage with alpha,beta-unsaturated acylazolium intermediates generated from enals by oxidative NHC catalysis to produce pyrrole-fused lactones in high yield and excellent enantioselectivity. Synthetic utility of the lactone products is also demonstrated by facile conversion to densely functionalized pyrroles and pyrrolin-4-ones in high yields with excellent stereopurity.
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关键词
Cascade Annulation, Cycloaddition, Enantioselectivity, Gold Catalysis, Relay Catalysis
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