4.8 Article

Copper-Catalyzed Enantioselective Cyclopropanation of Internal Olefins with Diazomalonates

Journal

ORGANIC LETTERS
Volume 19, Issue 21, Pages 5717-5719

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02694

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Funding

  1. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
  2. Youth Innovation Promotion Association CAS [2017301]
  3. Start-up Research Fund of Nanjing Agricultural University [050-804099]
  4. Fundamental Research Funds for the Central Universities [KYTZ201604]

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The first enantioselective copper catalyzed cyclopropanation of internal olefins with diazomalonates is reported. This process provides a new method for the synthesis of chiral 1,1-cyclopropane diesters. With a chiral bi-side arm bisoxazoline copper(I) complex, the reaction performed well over a series of substrates, giving the desired products in good yields (up to 95%) and excellent enantioselectivities (90-95% ee).

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