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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
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.