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N,N′ ‐Dioxide–Scandium(III)‐Catalyzed Asymmetric Michael Addition of β,γ‐Unsaturated Butenolides to α,β‐Unsaturated γ‐Keto Esters
Author(s) -
Ji Jie,
Lin Lili,
Zhou Lin,
Zhang Yuheng,
Liu Yangbin,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2013
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.201300586
Subject(s) - chemistry , scandium , butenolide , catalysis , michael reaction , lactone , organic chemistry , medicinal chemistry
A highly efficient N,N′ ‐dioxide–scandium(III) complex catalytic system has been developed for the asymmetric vinylogous Michael reaction of α‐angelica lactone and its derivatives to α,β‐unsaturated γ‐keto esters, affording the corresponding γ,γ‐disubstituted butenolide products in moderate to good yields (up to 93%) with high dr (up to >19:1) and ee values (up to 97%) under mild reaction conditions.