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Synfacts 2005(2): 0228-0228  
DOI: 10.1055/s-2005-916107
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Chiral Lithium Binaphtholate Aqua Complex for Cyanohydrin Synthesis

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

Publication Date:
25 October 2005 (online)

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Significance

Cyanohydrin synthesis has become a widely studied area for asymmetric synthesis. This report describes a Lewis base (binaphtholate) catalyzed reaction between aromatic aldehydes and TMSCN. Relatively low catalyst loadings (<10 mol%), with short reaction times were sufficient to give enantiomeric excesses exceeding 90% in many cases. Good results were obtained on large scale and with a minimum of solvent (5 M in some cases).