4.8 Article

Nickel-Catalyzed Asymmetric Transfer Hydrogenation of Olefins for the Synthesis of α- and β-Amino Acids

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 45, Pages 12210-12213

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201407744

Keywords

amino acids; hydride insertion; formic acid; nickel; transfer hydrogenation

Funding

  1. Singapore GSK-EDB Green
  2. Sustainable Manufacturing Award
  3. Nanyang Technological University

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The field of asymmetric (transfer) hydrogenation of prochiral olefins has been dominated by noble metal catalysts based on rhodium, ruthenium, and iridium. Herein we report that a simple nickel catalyst is highly active in the transfer hydrogenation using formic acid. Chiral alpha- and beta-amino acid derivatives were obtained in good to excellent enantioselectivity. The key toward success was the use of the strongly donating and sterically demanding bisphosphine Binapine.

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