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Synfacts 2006(10): 1025-1025  
DOI: 10.1055/s-2006-949340
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Dialkylzinc Addition to Aldehydes Catalyzed by Chiral Zn(II)-BINOLates

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
M. Hatano, T. Miyamoto, K. Ishihara*
Nagoya University, Japan
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Publication History

Publication Date:
21 September 2006 (online)

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Significance

The group describes an advance in the efficiency for the addition of dialkyl zinc reagents to aldehydes. The synthesis of BINOL ligands with phosphonate and phosphoramide appendages at the 3,3′-position led to enhanced reactivity allowing for lower ligand loading as well as a reduction in the amount of dialkylzinc used. The ee values obtained as well as the yields of the chiral alcohols are extremely high.