The fate of the tert-butylsulfinyl auxiliary after acid-promoted cleavage-a method for recycling t-BuSONH2

Varinder K. Aggarwal*, Nekane Barbero, Eoghan M. McGarrigle, Greg Mickle, Raquel Navas-Garcia, Jose Ramon Suarez-Alvarez, Matthew G. Unthank, Muhammad Yar

*Corresponding author for this work

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

40 Citations (Scopus)

Abstract

Ellman's chiral auxiliary is converted into tert-butylsulfinyl chloride on sulfinamide deprotection with HCl and can be recovered in high yield upon treatment with ammonia. The enantiopure auxiliary can be obtained by trapping the sulfinyl chloride with a chiral alcohol followed by treatment of the resulting sulfinate ester with LiNH2. (C) 2009 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)3482-3484
Number of pages3
JournalTetrahedron Letters
Volume50
Issue number26
DOIs
Publication statusPublished - 1 Jul 2009

Keywords

  • Ellman's auxiliary
  • tert-Butylsulfinamide
  • Sulfinimines
  • Deprotection
  • Cleavage
  • Dynamic kinetic resolution
  • DYNAMIC KINETIC RESOLUTION
  • ASYMMETRIC-SYNTHESIS
  • SULFINYL CHLORIDES
  • BUTANESULFINYL IMINES
  • BIS-SULFOXIDES
  • AMINES
  • DAG
  • SULFINIMINES
  • COMBINATIONS
  • SULFINAMIDES

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