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Asymmetric amplification in catalysis by trans-1,2-diaminocyclohexane bistriflamide
Tummanapalli Satyanarayana1, Benoit Ferber, Henri B Kagan
1Laboratoire de Catalyse Moléculaire (UMR 8182), Institut de Chimie Moléculaire et des Matériaux d'Orsay, Université Paris-Sud, 91405 Orsay, France.
Abstract:
A strong asymmetric amplification is observed in the addition of diethylzinc on aromatic aldehydes in the presence of the bistriflamide of trans-1,2-diaminocyclohexane 3a. The asymmetric amplification originates from the insolubility of the catalyst precursor 3a of low enantiomeric excess (ee), with a concomitant large increase of ee for the minor soluble part of 3a. Controlled mono-N-acetylation of 3a (20% ee) at -78 degrees C allowed isolation of 4 possessing 90% ee. [reaction: see text].
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