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N‐Heterocyclic Carbene Catalyzed Formal [3+2] Annulation Reaction of Enals: An Efficient Enantioselective Access to Spiro‐Heterocycles
Author(s) -
Guo Chang,
Schedler Michael,
Daniliuc Constantin G.,
Glorius Frank
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201405381
Subject(s) - stereocenter , annulation , enantioselective synthesis , carbene , catalysis , chemistry , organocatalysis , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry
A highly enantioselective N‐heterocyclic carbene (NHC) catalyzed formal [3+2] annulation of α,β‐unsaturated aldehydes with azaaurones or aurone generating spiro‐heterocycles has been developed. The protocol represents a unique NHC‐activation‐based approach to access spiro‐heterocyclic derivatives bearing a quaternary stereogenic center with high optical purity (up to 95 % ee ).