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Enantioselective N‐Heterocyclic Carbene Catalysis that Exploits Imine Umpolung
Author(s) -
Fernando Jared E. M.,
Nakano Yuji,
Zhang Changhe,
Lupton David W.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201812585
Subject(s) - umpolung , imine , enantioselective synthesis , carbene , chemistry , organocatalysis , catalysis , combinatorial chemistry , organic chemistry , nucleophile
The catalytic umpolung of imines remains an underdeveloped approach to reaction discovery. Herein we report an enantioselective aza‐Stetter reaction that proceeds via imine umpolung using N‐heterocyclic carbene catalysis. The reaction proceeds with high levels of enantioselectivity (all ≥96:4 er) and good generality (21 examples). Mechanistic studies are reported and are consistent with turnover‐limiting addition of the NHC to the imine.