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Letter

Aminohydroxyphosphine Ligand for the Copper-Catalyzed Enantioselective Conjugate Addition of Organozinc Reagents

Supporting Info

Alakananda Hajra, Naohiko Yoshikai, and Eiichi Nakamura*

Department of Chemistry, The University of Tokyo, Bunkyo-ku, Tokyo 113-0033, Japan

Org. Lett., 2006, 8 (18), pp 4153–4155

DOI: 10.1021/ol0618306

Publication Date (Web): August 8, 2006

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

, nakamura@chem.s.u-tokyo.ac.jp

Abstract

An alanine-derived aminohydroxyphosphine ligand was developed for copper-catalyzed asymmetric conjugate addition of organozinc reagents to α,β-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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History

Published In Issue August 31, 2006
Received July 25, 2006

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Letter

Aminohydroxyphosphine Ligand for the Copper-Catalyzed Enantioselective Conjugate Addition of Organozinc Reagents