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Synlett 2006(1): 0041-0044
DOI: 10.1055/s-2005-922757
DOI: 10.1055/s-2005-922757
LETTER
© Georg Thieme Verlag Stuttgart · New York
Reversal of Enantioselectivity by Catalyst Protonation: Asymmetric Hydrocyanation of Imines with Oxazaborolidines
Further Information
Publication History
Received
29 September 2005
Publication Date:
16 December 2005 (online)
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Abstract
A new application of chiral oxazaborolidines in asymmetric transformation, namely the hydrocyanation of imines, is described. The effect of protonation of these catalysts on the reactivity and enantioselectivity of hydrocyanations is studied. Significant increase in reaction rate is observed upon protonation of the catalysts, along with the reversal of the sense of stereoinduction.
Key words
oxazaborolidine - asymmetric catalysis - hydrocyanation - imine - protonation