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

  1. Varinder K. Aggarwal 1
  2. Nekane Barbero 1
  3. Eoghan M. McGarrigle 1
  4. Greg Mickle 1
  5. Raquel Navas 1
  6. José Ramón Suárez 1
  7. Matthew G. Unthank 1
  8. Muhammad Yar 1
  1. 1 School of Chemistry, University of Bristol, Cantock’s Close, Bristol BS8 1TS, UK
Revista:
Tetrahedron Letters

ISSN: 0040-4039

Año de publicación: 2009

Volumen: 50

Número: 26

Páginas: 3482-3484

Tipo: Artículo

DOI: 10.1016/J.TETLET.2009.03.020 GOOGLE SCHOLAR lock_openAcceso abierto editor

Otras publicaciones en: Tetrahedron Letters

Resumen

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.

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