Volume 39, Issue 16 pp. 2863-2866
Communication

A Simple Model for the Origin of Enantioselection and the Anti “Lock-and-Key” Motif in Asymmetric Hydrogenation of Enamides as Catalyzed by Chiral Diphosphine Complexes of Rh(I)

Clark R. Landis Prof.

Clark R. Landis Prof.

Department of Chemistry University of Wisconsin-Madison 1101 University Avenue Madison, WI 53706 (USA) Fax: (+1) 608-262-6143

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Steven Feldgus Steven

Steven Feldgus Steven

Department of Chemistry University of Wisconsin-Madison 1101 University Avenue Madison, WI 53706 (USA) Fax: (+1) 608-262-6143

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This work was supported by the National Science Foundation (CHE-9618497) and by the National Center for Supercomputer Applications under MCA99S017N and used the CRAY ORIGIN 2000 computer system at the NCSA.

Abstract

Hybrid molecular orbital/molecular mechanics calculations are used to determine the origin of the “anti-lock-and-key” behavior in asymmetric catalytic hydrogenation. The computations provide a simple model to explain this behavior (see scheme), and agree with all relevant empirical data.

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