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40.11 Product Class 11: Amido Derivatives of Sulfurous Acid

DOI: 10.1055/sos-SD-040-00963

Chemler, S. R.Science of Synthesis, (2009401269.

General Introduction

Amido derivatives of sulfurous acid are useful reagents in organic synthesis as well as compounds with demonstrated biological activity. For example, (alkylamino)sulfinyl chlorides have been used to install 5-hydroxy-protecting groups in deoxyribonucleosides for solid-phase DNA synthesis.[‌1‌] N,N-Diethylaminosulfur trifluoride (DAST) has demonstrated broad utility as a fluorinating agent,[‌2‌] and N-sulfinylalkanamines and N,N-dialkylsulfur diimides are electrophilic compounds that undergo nucleophilic addition reactions[‌3‌‌5‌] as well as pericyclic reactions such as DielsAlder[‌6‌‌13‌] and ene[‌14‌‌19‌] reactions. N,N-Sulfinylalkanamines have demonstrated bacteriostatic[‌20‌,‌21‌] and anticancer activity[‌22‌] and have been examined in the context of anti-HIV therapy.[‌23‌]