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, José Ramón Suárez, Matthew G. Unthank, Muhammad Yar

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

43 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.

Original languageEnglish
Pages (from-to)3482-3484
Number of pages3
JournalTetrahedron Letters
Volume50
Issue number26
Early online date10 Mar 2009
DOIs
Publication statusPublished - 1 Jul 2009
Externally publishedYes

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