1,4-Dithiane-2,5-diol as an efficient synthon for a straightforward synthesis of functionalized tetrahydrothiophenes via sulfa-Michael/aldol-type reactions with electrophilic alkenes

• DOI: 10.1016/j.tet.2011.10.064
• Publication Date: 2011-10-25T22:36:40Z
• Authors: Nikla Baricordi; Simonetta Benetti; Valerio Bertolasi; Carmela De Risi; Gian P. Pollini; Francesco Zamberlan; Vinicio Zanirato
• Keywords: Tetrahydrothiophene; Aldol reaction; Dithiane; Synthon; Michael reaction

Abstract ‘One-pot’ tandem reactions of commercially available 1,4-dithiane-2,5-diol (the dimer of mercaptoacetaldehyde) with electrophilic alkenes resulted in the facile formation of substituted tetrahydrothiophene derivatives. Thus, sulfa-Michael/Henry and sulfa-Michael/aldol sequences provided polysubstituted tetrahydrothiophenes using in situ generated nitroalkenes and α,β-unsaturated carbonyl compounds as the electrophilic partners of mercaptoacetaldehyde dimer, respectively.