4.8 Article

Copper-Catalyzed Diastereo- and Enantioselective Desymmetrization of Cyclopropenes: Synthesis of Cyclopropylboronates

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 45, Pages 15833-15836

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja510419z

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Funding

  1. European Research Council [ERC-337776]
  2. MINECO [CTQ2012-35957]
  3. MICINN

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A novel Cu-catalyzed diastereo- and enantioselective desymmetrization of cyclopropenes to afford nonracemic cyclopropylboronates is described. Trapping the cyclopropylcopper intermediate with electrophilic amines allows for the synthesis of cyclopropylaminoboronic esters and demonstrates the potential of the approach for the synthesis of functionalized cyclopropanes.

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