4.8 Article

A Highly Enantioselective Hydrogenation of Silyl Enol Ethers Catalyzed by Chiral Frustrated Lewis Pairs

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 35, Pages 12261-12264

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja507536n

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Funding

  1. National Basic Research Program of China (973 Program) [2010CB833300]
  2. National Natural Science Foundation of China [20802079, 21222207]

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Using a simple combination of tri-tert-butylphosphine and chiral borane generated in situ by the hydroboration of chiral diene with HB(C6F5)(2) as a frustrated Lewis pair catalyst, a highly enantioselective metal-free hydrogenation of silyl enol ethers was successfully realized to furnish a variety of optically active secondary alcohols in 93-99% yields with 88->99% ee's.

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