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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201506701
Subject(s) - stereocenter , conjugate , chemistry , catalysis , enantioselective synthesis , intermolecular force , quaternary carbon , combinatorial chemistry , brønsted–lowry acid–base theory , carbon fibers , organocatalysis , organic chemistry , molecule , materials science , mathematics , composite number , composite material , mathematical analysis
Abstract 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.