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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

By N. Baricordi, S. Benetti, V. Bertolasi, C. De Risi, G. P. Pollini, F. Zamberlan and V. Zanirato


‘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 alpha,beta-unsaturated carbonyl compounds as the electrophilic partners of mercaptoacetaldehyde dimer, respectively

Topics: Tandem reactions, Sulfa-Michael reactions, Sulfur heterocycles, Tetrahydrothiophenes
Year: 2012
DOI identifier: 10.1016/j.tet.2011.10.064
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