Highly enantioselective oxidations of ketene dithioacetals leading to trans bis-sulfoxides

VK Aggarwal*, RM Steele, Ritmaleni Ritmaleni, Juliet K Barrell, Ian Grayson

*Corresponding author for this work

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

28 Citations (Scopus)

Abstract

Ketene dithioacetals undergo a Sharpless-type asymmetric oxidation using (+)-DET, Ti((OPr)-Pr-i)(4), and cumene hydroperoxide to give the trans bis-sulfoxides 4a-f with essentially complete control of enantioselectivity and diastereoselectivity. The high enantioselectivity is a consequence of carrying out two asymmetric processes on the same substrate. However, this should lead to the formation of a small amount of the meso isomer but none was isolated. From monitoring the enantioselectivity of the monoxide over time, it was concluded that small amounts of the meso isomer must be formed. The inability to isolate this compound could be because it acted as a ligand on titanium and remained tightly bound even upon workup.

Original languageEnglish
Pages (from-to)4087-4090
Number of pages4
JournalJournal of Organic Chemistry
Volume68
Issue number10
DOIs
Publication statusPublished - 16 May 2003

Keywords

  • ASYMMETRIC-SYNTHESIS
  • ORGANIC-SYNTHESIS
  • (1R,3R)-2-METHYLENE-1,3-DITHIOLANE 1,3-DIOXIDE
  • TRANS-1,3-DITHIANE 1,3-DIOXIDE
  • CYCLOADDITION REACTIONS
  • 4+2 CYCLOADDITIONS
  • EQUIVALENT
  • EPOXIDATION
  • THIOACETALS
  • DIOXIDES

Cite this