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手性钯/铱配合物协同催化的多取代螺环戊烷吲哚醇的对映选择性合成。

Enantioselective Synthesis of Multisubstituted Spirocyclopentane Oxindoles Enabled by Pd/Chiral Rh(III) Complex Synergistic Catalysis.

机构信息

College of Chemistry, Fuzhou University, Fuzhou 350108, P. R. China.

State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou 350002, P. R. China.

出版信息

Org Lett. 2020 Dec 18;22(24):9539-9544. doi: 10.1021/acs.orglett.0c03588. Epub 2020 Dec 2.

Abstract

An asymmetric [3 + 2]-cycloaddition reaction of α,β-unsaturated 2-acyl imidazoles with spirovinylcyclopropanyl-2-oxindoles catalyzed synergistically by an achiral palladium(0) catalyst and a chiral-at-metal rhodium(III) complex has been developed. A series of biologically important 3-spirocyclopentane-2-oxindoles with four contiguous stereocenters were synthesized in high yields (up to 99%) with excellent stereoselectivities (up to 99% ee, 20:1 dr).

摘要

一种不对称的[3+2]环加成反应,α,β-不饱和 2-酰基咪唑与螺环乙烯基环丙基-2-氧吲哚在非手性钯(0)催化剂和手性金属铑(III)配合物的协同作用下发生反应。一系列具有重要生物活性的 3-螺环戊烷-2-氧吲哚,其中含有四个连续的立体中心,以高产率(高达 99%)和优异的立体选择性(高达 99%ee,20:1dr)合成。

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