Journals Proceedings

Abstract

The cyclic thionocarbamate of alaninol undergoes nucleophilic attack at 5-C by sulfur nucleophiles when derivatised on nitrogen with a Boc group, to reduce nitrogen to thione conjugation, to give 2-thioethylamine derivatives. Iodide under microwave conditions causes a rearrangement to the thiazolidinone. “Hard” nucleophiles react at the thione group followed by either C-N or C-O cleavage to yield a variety of product types.