‘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.

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
Primo
;
BENETTI, Simonetta
Secondo
;
BERTOLASI, Valerio;DE RISI, Carmela
;
POLLINI, Gian Piero;ZAMBERLAN, Francesco
Penultimo
;
ZANIRATO, Vinicio
Ultimo
2012

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 alpha,beta-unsaturated carbonyl compounds as the electrophilic partners of mercaptoacetaldehyde dimer, respectively.
Baricordi, Nikla; Benetti, Simonetta; Bertolasi, Valerio; DE RISI, Carmela; Pollini, Gian Piero; Zamberlan, Francesco; Zanirato, Vinicio
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11392/1595265
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