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Synfacts 2006(10): 1041-1041  
DOI: 10.1055/s-2006-949274
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Zn(II)-Catalyzed Mannich-Type Reactions of Enolizable Imines

Contributor(s): Mark Lautens, Andrew Martins
A. Yamaguchi, S. Matsunaga*, M. Shibasaki*
The University of Tokyo, Japan
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Publikationsdatum:
21. September 2006 (online)

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Significance

Using a dinuclear Zn(II)/BINOL-based catalyst, a variety of enolizable N-diphenyl­phosphinoyl (N-DPP) imines underwent a selective Mannich-type reaction with an α-hydroxyketone to generate chiral amino alcohols. Diastereo-selectivity was the main limitation, as poor to fair syn/anti ratios were reported, although enantio­selectivities were excellent for each diastereomer.