Premium
Enantioselective Synthesis of Chromanones via a Tryptophan‐ Derived Bifunctional Thiourea‐Catalyzed Oxa‐Michael–Michael Cascade Reaction
Author(s) -
Wang Haifei,
Luo Jie,
Han Xiao,
Lu Yixin
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.201100419
Subject(s) - michael reaction , chemistry , bifunctional , thiourea , enantioselective synthesis , catalysis , amine gas treating , organocatalysis , organic chemistry , cascade reaction , tertiary amine
Tryptophan‐derived tertiary amine‐thiourea catalysts were shown to promote a cascade oxa‐Michael–Michael reaction between ethylene β‐keto esters and nitroolefins, resulting in the formation of 3,3‐disubstituted 4‐chromanones bearing a quaternary center in high diastereoselectivity and enantioselectivity. The chromanone products can be readily converted to biologically important fused and spiro tricyclic chromans.