4.6 Article

Highly Enantioselective Copper-Catalyzed Ring Opening of Oxabicyclic Alkenes with Grignard Reagents

Journal

CHEMISTRY-AN ASIAN JOURNAL
Volume 3, Issue 12, Pages 2105-2111

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.200800159

Keywords

asymmetric catalysis; copper; enantioselectivity; Grignard reaction; spiro compounds

Funding

  1. National Natural Science Foundation of China [20532010, 20702025]
  2. Major Basic Research Development Program [2006CB806106]
  3. Ministry of Education of China [1306005]

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A highly efficient copper-catalyzed enantioselective ring opening of oxabicylic alkenes with Grignard reagents has been developed by using chiral spiro phosphine ligands. Excellent trans selectivities, good yields, and high enantioselectivities are obtained for a broad range of Grignard reagents under mild reaction conditions. The catalyst system shows an extraordinary activity and the TON of the reaction reaches 9000.

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