4.8 Article

Highly Diastereo- and Enantioselective Pd-Catalyzed Cyclopropanation of Acyclic Amides with Substituted Allyl Carbonates

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 25, Pages 8734-+

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja902410w

Keywords

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Funding

  1. Major Basic Research Development Program [2006CB806106]
  2. National Natural Science Foundation of China [20532050, 20672130, 20821002]
  3. Chinese Academy of Sciences, Shanghai Committee of Science and Technology
  4. Croucher Foundation of Hong Kong

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A highly diastereo- and enantioselective cyclopropanation reaction was realized in the reaction of acyclic amides with monosubstituted allyl carbonates via Pd-catalysis using a ferrocene ligand with H as a substituent on an oxazoline ring, providing cyclopropane products having three chiral centers in yields of 67-83%, the dr ratio being 4-23:1, and ee being 83-97%. The presence of LiCl is important for the gain of high diastereo- and enantioselectivities of the reaction.

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