Tandem Chemoselective 1,2-/1,4-Migration of the Thio Group in Keto Thioesters: An Efficient Approach to Substituted Butenolides

Kanchan Mal, Sandip Naskar, Shovan Kumar Sen, Ramalingam Natarajan, Indrajit Das

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

Abstract

We report herein an efficient and mechanistically unique tandem chemoselective 1,2-/1,4-migration of the thio group in keto thioesters that provides substituted butenolides in moderate to excellent yields. Thus, α-keto thioesters in the presence of stabilized phosphonate carbanions undergo tandem 1,2-sulfur migration; whereas 1,4-migration of the thio group has been achieved with the same thioesters after the treatment with Wittig reagents followed by BF3⋅OEt2-catalyzed tandem reaction. The crossover experiments and the isolation of intermediates reveal a stepwise mechanism for both of these transformations. (Figure presented.).

Original languageEnglish
Pages (from-to)3212-3230
Number of pages19
JournalAdvanced Synthesis and Catalysis
Volume358
Issue number20
DOIs
StatePublished - 20 Oct 2016
Externally publishedYes

Keywords

  • heterocycles
  • isomerization
  • keto thioesters
  • rearrangement
  • sulfanyl group migration

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Tandem Chemoselective 1,2-/1,4-Migration of the Thio Group in Keto Thioesters: An Efficient Approach to Substituted Butenolides'. Together they form a unique fingerprint.

Cite this