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

Baricordi, Nikla and Benetti, Simonetta and Bertolasi, Valerio and De Risi, Carmela and Pollini, Gian P. and Zamberlan, Francesco and Zanirato, Vinicio (2012) 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. Tetrahedron, 68 (1). pp. 208-213. ISSN 0040-4020

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Item Type:Article
Item Status:Live Archive

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 a,b-unsaturated carbonyl compounds as
the electrophilic partners of mercaptoacetaldehyde dimer, respectively.

Keywords:organic chemistry, organic synthesis, heterocycles, sulfur
Subjects:F Physical Sciences > F151 Pharmaceutical Chemistry
F Physical Sciences > F160 Organic Chemistry
F Physical Sciences > F150 Medicinal Chemistry
Divisions:College of Science > School of Chemistry
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ID Code:30365
Deposited On:09 Mar 2018 12:22

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