Application of the chiral acyl anion equivalent, trans-1,3-dithiane 1,3-dioxide, to an asymmetric synthesis of (R)-salbutamol

VK Aggarwal*, Blanca N Esquivel Zamora

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

16 Citations (Scopus)

Abstract

An enantioselective synthesis of (R)-salbutamol has been carried out using the chiral, C-2\ symmetric acyl anion equivalent, (1-R,3R)-1,3-dithiane 1,3-dioxide, which undergoes addition to an aromatic aldehyde with very high stereocontrol at 0 degreesC. Pummerer reaction and work-up with lithium ethanethiolate generated the alpha-hydroxy thiolester in high yield and further transformations led to the target compound with high enantiomeric excess.

Original languageEnglish
Pages (from-to)8618-8621
Number of pages4
JournalJournal of Organic Chemistry
Volume67
Issue number24
DOIs
Publication statusPublished - 29 Nov 2002

Keywords

  • ENANTIOSELECTIVE SYNTHESIS
  • OXAZABOROLIDINE CATALYSTS
  • REDUCTION
  • DERIVATIVES
  • ACIDS

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