A general method for the preparation of N-sulfonyl aldimines and ketimines

Org Lett. 2005 Jan 20;7(2):179-82. doi: 10.1021/ol048005e.

Abstract

[Reaction: see text] A simple procedure to obtain N-sulfonyl imines involving the condensation of carbonyl compounds with p-tolyl or tert-butyl sulfinamides followed by oxidation with m-CPBA of the resulting N-sulfinylimines is reported. The method is applicable to aldehydes (aliphatics and aromatics) and ketones (diaryl, dialkyl, and aryl alkyl), even those containing enolizable protons. It also does not affect C=N or C=C double bonds and does not epimerize alpha-stereogenic centers.