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

Research output: Contribution to journalArticlepeer-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 languageEnglish (US)
Pages (from-to)1087-1089
Number of pages3
JournalSynlett
Volume1997
Issue number9
DOIs
StatePublished - Jan 1 1997

ASJC Scopus subject areas

  • Organic Chemistry

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