Highly enantio- and diastereoselective vinylogous aldol reaction by LiCl-assisted BINOL-titanium species

Org Lett. 2012 Jun 1;14(11):2734-7. doi: 10.1021/ol300946j. Epub 2012 May 23.

Abstract

The first highly enantio- and diastereoselective vinylogous aldol reaction between propionyl acetate-derived Brassard's diene and aldehydes was accomplished by titanium-lithium combined Lewis acid, affording δ-hydroxy-γ-methyl-β-methoxy acrylates. This methodology was utilized in convenient and concise construction of the polypropionate moiety in cystothiazole A and melithiazole C.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Lithium Chloride / chemistry
  • Molecular Structure
  • Naphthols / chemistry
  • Stereoisomerism
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry
  • Titanium / chemistry*

Substances

  • Aldehydes
  • BINOL, naphthol
  • Naphthols
  • Thiazoles
  • cystothiazole A
  • 3-hydroxybutanal
  • Titanium
  • Lithium Chloride