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Regioselective and Enantioselective Domino Aldol–Oxa‐Michael Reactions to Construct Quaternary (Chroman) Stereocenters
Author(s) -
Liu Kegang,
Jiang Xiaohua
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501065
Subject(s) - stereocenter , regioselectivity , chemistry , enantioselective synthesis , aldol reaction , domino , michael reaction , organocatalysis , stereoselectivity , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
An asymmetric domino aldol–oxa‐Michael reaction of salicylaldehydes and β,β‐disubstituted α,β‐unsaturated aldehydes has been developed by using dienamine‐mediated catalysis. The developed strategy leading to the stereoselective and regioselective formation of novel chroman derivatives with quaternary (chroman) stereocenters is presented. Particularly, salicylaldehydes with variously substitution patterns dominate the efficient construction of the chroman derivatives with high molecular complexity and skeletal diversity in excellent diastereo‐ and enantioselectivities.