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Synfacts 2005(2): 0226-0226  
DOI: 10.1055/s-2005-916105
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Dual Lewis Acid-Lewis Base Activation in Enantioselective Cyanation of Aldehydes

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
S. Lundgren, E. Wingstrand, M. Penhoat, C. Moberg*
Royal Institute of Technology, stockholm, Sweden
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Publication History

Publication Date:
25 October 2005 (online)

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Significance

Asymmetric cyanation of aldehydes and ketones has been thoroughly studied due to the importance of the resulting cynaohydrin products. Often, the toxic and expensive TMS-cyanide has been the cyanide source and results in TMS- protected or free hydroxyl group products. This paper provides a route to enantiomerically pure oxygen-functionalized cyanide products giving yields in excess of 80% and enantioselectivities greater than 90% in many cases.