jo2025288_si_003.pdf (3.25 MB)
Asymmetric Michael Addition of α-Substituted Isocyanoacetates with Maleimides Catalyzed by Chiral Tertiary Amine Thiourea
journal contribution
posted on 2016-02-21, 17:25 authored by Jian-Fei Bai, Liang-Liang Wang, Lin Peng, Yun-Long Guo, Li-Na Jia, Fang Tian, Guang-Yun He, Xiao-Ying Xu, Li-Xin WangA highly diastereoselective and enantioselective Michael
addition
of α-substituted isocyanoacetates with maleimides catalyzed
by bifunctional tertiary amine thioureas has been developed. Various
chiral succinimide derivatives bearing adjacent quaternary and tertiary
stereocenters were prepared in excellent yields (up to 98%), diastereoselectivities
(up to 99:1), and enantioselectivities (up to 98% ee). The synthetic
utility of chiral succinimide derivatives is also demonstrated in
the preparation of h5-HT1d receptor agonist motifs.
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diastereoselectivemotifamine thioureasstereocentermaleimideIsocyanoacetateChiral Tertiary Amine ThioureaAAsymmetric Michael AdditiondiastereoselectivitieeeMaleimides CatalyzedisocyanoacetateutilityVarious chiral succinimide derivativeschiral succinimide derivativesenantioselectivitieenantioselective Michael additionbifunctionalagonistyieldpreparationquaternaryreceptorSubstituted
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