Enantioselective and Diastereoselective Construction of Chiral Amino Alcohols by Iridium-f-Amphox-Catalyzed Asymmetric Hydrogenation via Dynamic Kinetic Resolution

  • Org Lett. 2017 May 19;19(10):2548-2551. doi: 10.1021/acs.orglett.7b00844.
Weilong Wu  1 ,  Cai You  1 ,  Congcong Yin  1 ,  Yuanhua Liu  1 ,  Xiu-Qin Dong  1 ,  Xumu Zhang  1  2
Affiliations
  • 1. College of Chemistry and Molecular Sciences, Wuhan University , Wuhan, Hubei 430072, P. R. China.
  • 2. Department of Chemistry, South University of Science and Technology of China , Shenzhen, Guangdong 518055, P. R. China.
PMID: 28448152 DOI: 10.1021/acs.orglett.7b00844
Abstract

The iridium-f-amphox-catalyzed asymmetric hydrogenation of racemic α-amino β-unfunctionalized ketones proceeds via a DKR (dynamic kinetic resolution) process for the construction of various chiral N,N-disubstituted α-amino β-unfunctionalized alcohols in quantitative yields with excellent enantioselectivities and diastereoselectivities (all products >99% ee and >99:1 dr, TON up to 100 000). Importantly, this catalytic asymmetric hydrogenation with a DKR process provided a highly efficient and powerful synthetic strategy for the preparation of key chiral intermediates of the preclinical antitumor agent (S,S)-R116010.

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