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

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.