Aminohydroxyphosphine ligand for the copper-catalyzed enantioselective conjugate addition of organozinc reagents |
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Authors: | Hajra Alakananda Yoshikai Naohiko Nakamura Eiichi |
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Institution: | Department of Chemistry, University of Tokyo, Bunkyo-ku, Tokyo 113-0033, Japan. |
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Abstract: | An alanine-derived aminohydroxyphosphine ligand was developed for copper-catalyzed asymmetric conjugate addition of organozinc reagents to alpha,beta-unsaturated carbonyl compounds. This new tridentate ligand induces consistently high enantioselectivity in reactions of a variety of acyclic substrates. Theoretical mechanistic analysis suggests that the C-C bond formation takes place through a highly ordered transition state by the coordination of the phosphorus and nitrogen atoms to the copper(III) and zinc(II) atoms, respectively, and of the oxygen anion to both the metal centers. |
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