The Chemistry of Chlorosilyl Enolates 3.: Variation of the Silyl Group and the Effect on Rate and Enantiomeric Excess of Acetate Aldol Additions

Scott E. Denmark; Stephen B.D. Winter

doi:10.1055/s-1997-1543

The Chemistry of Chlorosilyl Enolates 3. Variation of the Silyl Group and the Effect on Rate and Enantiomeric Excess of Acetate Aldol Additions

Scott E. Denmark, Stephen B.D. Winter

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English (US)
Pages (from-to)	1087-1089
Number of pages	3
Journal	Synlett
Volume	1997
Issue number	9
DOIs	https://doi.org/10.1055/s-1997-1543
State	Published - 1997

ASJC Scopus subject areas

Organic Chemistry

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abstract = "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.",

author = "Denmark, {Scott E.} and Winter, {Stephen B.D.}",

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AB - 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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