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Highly Enantioselective Conjugate Addition–Cyclization Cascade Reaction of Malonates with o ‐Hydroxycinnamaldehydes: Asymmetric Synthesis of 4‐Substituted Chromanols
Author(s) -
Lee Yongcheon,
Seo Seung Woo,
Kim SungGon
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100324
Subject(s) - chemistry , enantioselective synthesis , conjugate , organocatalysis , cascade reaction , combinatorial chemistry , cascade , organic chemistry , catalysis , stereochemistry , mathematical analysis , mathematics , chromatography
Abstract The asymmetric organocatalytic conjugate addition–cyclization reaction of malonates with o ‐hydroxycinnamaldehydes, which affords 4‐substituted chroman‐2‐ols, has been established using a diphenylprolinol trimethylsilyl (TMS) ether as organocatalyst. The desired products were obtained with good to excellent yields and high enantioselectivities (up to >99% ee ). Synthetically useful chroman derivatives were formed after subsequent reactions.