Asymmetric Michael Addition of α-Substituted Isocyanoacetates with Maleimides Catalyzed by Chiral Tertiary Amine Thiourea
journal contributionposted on 21.02.2016, 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 Wang
A 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