4,4‘-Disubstituted BINAPs for Highly Enantioselective Ru-Catalyzed Asymmetric Hydrogenation of Ketones

Aiguo Hu, Helen L. Ngo, and Wenbin Lin*
Department of Chemistry, CB#3290, University of North Carolina, Chapel Hill, North Carolina 27599
Org. Lett., 2004, 6 (17), pp 2937–2940
DOI: 10.1021/ol048993j
Publication Date (Web): July 20, 2004
Copyright © 2004 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, wlin@unc.edu

Abstract

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A family of tunable precatalysts Ru(4,4‘-BINAP)(chiral diamine)Cl2 was synthesized and used for highly enantioselective hydrogenation of aromatic ketones. This result differs from previous chiral diphosphines that rely on the bis(xylyl)phosphino groups to control enantioselectivity. An X-ray structural study reveals that the bulky substituents on the 4,4‘-positions of BINAP can effectively create a suitable chiral pocket in the transition state and thus provide a new mechanism for the enantiocontrol in such a remarkable asymmetric catalytic process.

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History

  • Published In Issue August 19, 2004
  • Received June 1, 2004

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