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Halpern higher reactivity of the latter, compared with that of the predominant diastereomer, toward H . 2 Because the formation and dissociation of the catalyst-substrate adducts, and hence interconversion and equilibration of their diastereomeric forms, are rapid (compared with their reactions with H ) at ambient temperatures and H pressures, these two alternatives are kinetically indistinguishable under the usual catalytic conditions. The first of the above interpretations, which corresponds to the familiar "lock and key" concept that has been invoked so widely to explain the characteristically high selectivities of enzymic catalysts, initially appeared to be more attractive on conceptual grounds and was widely accepted.

Soc. 92, 5389. , and Kumada, M. (1978). In "Fundamental Research in Homogeneous Catalysis" (Y. Ishii and M. ), Vol. 2. Plenum, N e w York. Hayashi, T , and Kumada, M. (1982). Acc. Chem. Res. 15, 395. , and Kumada, M. (1982). J. Am. Chem. Soc. 104, 180. Kagan, Η. , Fiaud, J. C , Hoornaert, C , Meyer, D . , and Poulin, J. C. (1979). Bull. Soc. Chim. Belg. 88, 923. Vineyard, B. , Knowles, W. , Sabacky, M. , Bachman, G. , and WeinkaufT, O. J. (1977). J. Am. Chem. Soc. 99, 5946. , private communication.

Brunner, Η. , (1984). Angew. Chem. 94, 305. , Deshmukh, Μ. N. and Kagan, H. ,(1984). J. Am. Chem. Soc. 106, 8188. Dunach, E. and Kagan, Η. , (1985), Nouv. J. Chim. 9, 1. , and Kagan, Η. B. (1985). , in press. , and Suga, S. (1983). Chem. Lett. p. 913. 2 Asymmetric Catalytic Hydrogenation: Mechanism and Origin of Enantioselection Jack Halpern D e p a r t m e n t of C h e m i s t r y T h e University of C h i c a g o C h i c a g o , Illinois I. II. III. IV. V. VI. VII. VIII. IX. Introduction Approaches to the Elucidation of Mechanism Chiral Phosphine Ligands Effect of Substrate Structure Tracer Experiments Using D and H D Kinetic and Related Mechanistic Studies A.

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