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Doubly Stereocontrolled Asymmetric Aza‐Henry Reaction with in situ Generation of N ‐Boc‐Imines Catalyzed by Novel Rosin‐Derived Amine Thiourea Catalysts
Author(s) -
Jiang Xianxing,
Zhang Yifu,
Wu Lipeng,
Zhang Gen,
Liu Xing,
Zhang Hailong,
Fu Dan,
Wang Rui
Publication year - 2009
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.200900413
Subject(s) - chemistry , cinchona , catalysis , yield (engineering) , thiourea , amine gas treating , organic chemistry , enantioselective synthesis , organocatalysis , rosin , nitroaldol reaction , medicinal chemistry , resin acid , materials science , metallurgy
The doubly stereocontrolled organocatalytic aza‐Henry reaction of nitroalkanes to N ‐Boc‐imines generated in situ from a variety of substituted α‐amido sulfones was investigated for the first time, in general, affording the corresponding products with high to excellent yields (up to 93% yield) and enantioselectivities (up to 98% ee ), and satisfactory diastereoselectivies ( anti / syn up to 98:2). Furthermore, these organocatalysts based on rosin have been proved to be the very effective promoters for this catalytic asymmetric process along side the Cinchona alkaloid‐derived catalysts.