A Chiral Cagelike Copper(I) Catalyst for the Highly Enantioselective Synthesis of 1,1-Cyclopropane Diesters

Authors

  • Chao Deng,

    1. The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China)
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  • Dr. Li-Jia Wang,

    1. The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China)
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  • Jun Zhu,

    1. The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China)
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  • Prof. Dr. Yong Tang

    Corresponding author
    1. The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China)
    • The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China)
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  • We are grateful for the financial support from the Natural Sciences Foundation of China (nos. 21121062, 20932008, and 21072207), the Major State Basic Research Development Program (grant no. 2009CB825300), and the Chinese Academy of Sciences.

Abstract

original image

Triangulation method: The catalytic enantioselective cyclopropanation of multisubstituted olefins with phenyliodonium ylide malonate has been achieved in the presence of a chiral bisoxazoline copper(I) complex (see scheme). A wide range of substrates undergo the reaction to provide optically active 1,1-cyclopropane diesters in high yield with up to >99 % ee. A rationale for the enantioselective induction has been proposed.

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