4.8 Article

Formal Carbene Insertion into C-C Bond: Rh(I)-Catalyzed Reaction of Benzocyclobutenols with Diazoesters

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 8, Pages 3013-3015

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja500118w

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Funding

  1. 973 Program [2012CB821600]
  2. NSFC [21332002, 21272010, 21172005]

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A Rh(I)-catalyzed formal carbene insertion into C-C bond of benzocyclobutenols has been realized by employing diazoesters as carbene precursors. The product indanol derivatives were obtained in good yields and in diastereoselective manner under mild reaction conditions. All-carbon quaternary center is constructed at the carbenic carbon. This catalytic reaction involves selective cleavage of C-C bond, Rh(I) carbene insertion, and intramolecular aldol reaction.

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