The Chemistry of Chlorosilyl Enolates 3.: Variation of the Silyl Group and the Effect on Rate and Enantiomeric Excess of Acetate Aldol Additions
- 1 September 1997
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1997 (9) , 1087-1089
- https://doi.org/10.1055/s-1997-1543
Abstract
The rates of reaction of the silyl ketene acetals CH2=C(OMe)OSiCl2R (1a-d) with benzaldehyde and pivalaldehyde have been determined and follow the order R = H ~ Cl > Ph > Me. These reactions are promoted by catalytic amounts of a chiral phosphoramide; enantioselectivities of the products obtained show a high sensitivity towards variation of the silyl group. The reactions of the dialkyl substituted chlorosilyl enolates CH2=C(OMe)OsiClR2 (1e,f) with benzaldehyde are not promoted by HMPA.Keywords
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