Lewis base activation of Lewis acids. Vinylogous aldol reactions

Scott E. Denmark, Gregory L. Beutner

Research output: Contribution to journalArticlepeer-review

Abstract

A highly regioselective vinylogous aldol reaction catalyzed by SiCl4 and a chiral phosphoramide (R,R)-5, providing δ-hydroxy enones for a variety of aldehyde and dienol ether structures, has been developed. Low catalyst loadings (1 mol %) can be employed, giving the products in good yields, excellent enantioselectivities, and in some cases excellent anti diastereoselectivities. Both simple ester-derived dienol ethers as well as dioxanone-derived dienol ethers are employed. The observed regioselectivity is rationalized in terms of the sensitivity of the catalyst to the steric demands of the nucleophile.

Original languageEnglish (US)
Pages (from-to)7800-7801
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number26
DOIs
StatePublished - Jul 2 2003

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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