Stereoselective syn aldol reaction of the lithium ester enolate of ethyl N,N-dimethylglycine in the presence of triethylborane

Gunda I. George, Eyüp Akgün

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

Aldol condensation of acetaldehyde and benzaldehyde with the lithium ester enolate of ethyl N,N-dimethylglycine in the presence of one equivalent of triethylborane resulted in the formation of the corresponding 3-hydroxy-2-amino acid ester with excellent stereocontrol (>95% de ) for the formation of syn products. The stereochemical outcome of these reactions is rationalized via the selective formation of the (Z)-enolate of 1 in the presence of triethylborane.

Original languageEnglish (US)
Pages (from-to)5521-5524
Number of pages4
JournalTetrahedron Letters
Volume32
Issue number40
DOIs
StatePublished - Sep 30 1991

Keywords

  • Aldol
  • Ester Enolate
  • Glycine
  • Syn Selectivity
  • Triethylborane

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