Transition‐Metal‐Free Decarboxylative Propargylic Substitution/Cyclization with either Azolium Enolates or Acyl Anions | Zendy

Lu Shenci | Zendy; Ong JunYang | Zendy; Poh Si Bei | Zendy; Tsang Terence | Zendy; Zhao Yu | Zendy

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Transition‐Metal‐Free Decarboxylative Propargylic Substitution/Cyclization with either Azolium Enolates or Acyl Anions

Author(s) -

Lu Shenci,

Ong JunYang,

Poh Si Bei,

Tsang Terence,

Zhao Yu

Publication year - 2018

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201801340

Subject(s) - allene , chemistry , decarboxylation , catalysis , transition metal , carbene , substitution (logic) , reactive intermediate , combinatorial chemistry , organic chemistry , stereochemistry , medicinal chemistry , computer science , programming language

Abstract Presented herein is an unprecedented transition‐metal‐free propargylic substitution reaction with either azolium enolates or acyl anions, which are generated from aldehydes under N‐heterocyclic carbene catalysis. This new catalytic activation operates on readily available cyclic propargylic carbamates through decarboxylation, and generates reactive allene intermediates that can undergo divergent cyclization pathways to deliver skeletally diverse polycyclic compounds with high levels of efficiency and excellent enantioselectivities.

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