Ring-opening reaction of Bus- and SES-protected aziridines using lithiated dithianes

Abstract

The scope and limitation of the ring-opening reaction of sulfonyl-activated aziridines using lithiated dithianes was investigated. Nucleophilic attack of lithiated dithianes on aziridines containing tert-butylsulfonyl (Bus) and 2-(trimethylsilyl)ethylsulfonyl (SES) demonstrated efficient ring cleavage to yield β-amino carbonyl equivalents, γ-lactam and syn- and anti-1,5-aminoalcohols. The first example of a ring-opening reaction of di-substituted aziridine using dithiane is also reported. Finally, the Bus and SES-possessing dithianes obtained were deprotected to demonstrate their synthetic usefulness.