Synlett p. 1087 - 1089 (1997)
Update date:2022-08-17
Topics:
Denmark, Scott E.
Winter, Stephen B. D.
The rales 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.
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