Enantioselective organocatalytic aldehyde-aldehyde cross-aldol couplings. The broad utility of α-thioacetal aldehydes

R. Ian Storer, David W.C. MacMillan

Research output: Contribution to journalArticlepeer-review

91 Scopus citations

Abstract

An asymmetric proline catalyzed aldol reaction with α-thioacetal aldehydes has been developed. Thioacetal bearing aldehydes readily participate as electrophilic cross-aldol partners with a broad range of aldehyde and ketone donors. High levels of reaction efficiency as well as diastereo- and enantiocontrol are observed in the production of anti-aldol adducts.

Original languageEnglish (US)
Pages (from-to)7705-7714
Number of pages10
JournalTetrahedron
Volume60
Issue number35
DOIs
StatePublished - Aug 23 2004
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Keywords

  • Aldol
  • Catalysis
  • Diastereoselection
  • Enantioselective
  • Organocatalysis
  • Proline

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