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Catalytic Asymmetric 1,6‐Conjugate Addition of para ‐Quinone Methides: Formation of All‐Carbon Quaternary Stereocenters
Author(s) -
Wang Zhaobin,
Wong Yuk Fai,
Sun Jianwei
Publication year - 2015
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.201506701
Subject(s) - stereocenter , conjugate , catalysis , quaternary carbon , chemistry , quinone , quaternary , carbon fibers , enantioselective synthesis , stereochemistry , organic chemistry , combinatorial chemistry , materials science , mathematics , biology , composite number , mathematical analysis , paleontology , composite material
Described herein is a general and mild catalytic asymmetric 1,6‐conjugate addition of para ‐quinone methides ( p ‐QMs), a class of challenging reactions with previous limited success. Benefiting from chiral Brønsted acid catalysis, which allows in situ formation of p ‐QMs, our reaction expands the scope to general p ‐QMs with various substitution patterns. It also enables efficient intermolecular formation of all‐carbon quaternary stereocenters with high enantioselectivity.