Preparation of bis(β-trimethylsilylethanesulfonyl)imide and its use in the synthesis of protected amine derivatives

David M. Dastrup, Michael P. VanBrunt, Steven M. Weinreb

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

Bis(β-trimethylsilylethanesulfonyl)imide (SES2-NH) can be easily prepared in 85% yield by alkylation of the trianion of bismethanesulfonimide with 2 equiv of commerically available (iodomethyl)trimethylsilane. This synthon undergoes effective Mitsunobu alkylation reactions with both primary and secondary alcohols to afford the corresponding bis-SES imides. These imides can be selectively cleaved to the mono-SES-protected amines, and in addition undergo a one-pot cleavage/N-alkylation to afford SES derivatives of secondary amines.

Original languageEnglish (US)
Pages (from-to)4112-4115
Number of pages4
JournalJournal of Organic Chemistry
Volume68
Issue number10
DOIs
StatePublished - May 16 2003

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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