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手性双功能奎宁生物碱衍生的酰亚胺/AgSbF6 协同催化α-芳基异氰基酯与 N-芳基马来酰亚胺的不对称[3+2]环加成反应。

Asymmetric formal [3+2] cycloaddition reaction of α-aryl isocyanoesters with N-aryl maleimides by bifunctional cinchona alkaloids-based squaramide/AgSbF6 cooperative catalysis.

机构信息

Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, PR China.

出版信息

Chem Asian J. 2012 Dec;7(12):2777-81. doi: 10.1002/asia.201200686. Epub 2012 Sep 24.

DOI:10.1002/asia.201200686
PMID:23002007
Abstract

It is better to be cooperative: A highly diastereo- and enantioselective asymmetric [3+2] cycloaddition reaction of α-aryl isocyanoacetates with N-aryl maleimides through cooperative catalysis of cinchona alkaloid-derived squaramide/AgSbF(6) was developed. A wide range of optically active, substituted 1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c] pyrrole derivatives was obtained in high yields (up to 98%), high diastereoselectivities (>20:1 d.r.), and good to excellent enantioselectivities (up to 92% ee) under mild reaction conditions.

摘要

通过金鸡纳生物碱衍生的手性联萘二胺/AgSbF6 协同催化,开发了一种高非对映选择性和对映选择性的不对称[3+2]环加成反应,用于α-芳基异氰基乙酸酯与 N-芳基马来酰亚胺的反应。在温和的反应条件下,以高产率(高达 98%)、高非对映选择性(>20:1 d.r.)和优异的对映选择性(高达 92%ee)得到了广泛的光学活性、取代的 1,3a,4,5,6,6a-六氢吡咯并[3,4-c]吡咯衍生物。

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