N‐Heterocyclic Carbene‐Catalyzed Atroposelective Synthesis of 5‐Indo‐1‐yl Pyran‐2‐ones with an N−C axis from Enals

Linxue Zhang,Qianqian Wu, Min Ren,Hailong Zhang,Xiaoxiang Zhang,Jinhua Liu,Zhenqian Fu

Advanced Synthesis and Catalysis（2023）

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摘要

A variety of 5-indo-1-yl pyran-2-ones with an N-C axis were prepared via a carbene-catalyzed oxidative [3+3] annulation of indole-1-pyruvate esters and enals. Asymmetric construction of pyran-2-one ring from enals ensures the realization of this strategy. The resulting compounds were converted into axially chiral N-arylindoles with an N-C axis via a cycloaddtion aromatization.

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关键词

Asymmetric catalysis,N-heterocyclic carbene,C−N axis,α,β-unsaturated aldehyde,N-arylindoles

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