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Synfacts 2006(9): 0926-0926  
DOI: 10.1055/s-2006-949264
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Ti(IV)/N-Oxide-Catalyzed Cyanosilylation of Ketones

Contributor(s): Mark Lautens, Andrew Martins
Q. Li, X. Liu, J. Wang, K. Shen, X. Feng*
Sichuan University, Chengdu, P. R. of China
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

Using a Ti(Oi-Pr)4/N,N′-dioxide catalyst system, a variety of chiral O-trimethylsilyl cyanohydrins are accessed by addition of Me3SiCN to methyl ketones. The yields are good to excellent, and enantioselectivities are good to very good. The advantage of this method is that the ligand is easily prepared from proline, and the catalyst system uses an inexpensive metal source. Interestingly, the addition of an achiral N-oxide additive improved both yield and enantioselectivity of the products.