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

被引：38

作者：

Baricordi, Nikla ^{[2
]}

Benetti, Simonetta ^{[2
]}

Bertolasi, Valerio ^{[2
]}

De Risi, Carmela ^{[1
]}

Pollini, Gian P. ^{[1
]}

Zamberlan, Francesco ^{[2
]}

Zanirato, Vinicio ^{[1
]}

机构：

[1] Dipartimento Sci Farmaceut, I-44121 Ferrara, Italy

[2] Dipartimento Chim, I-44121 Ferrara, Italy

来源：

TETRAHEDRON | 2012年 / 68卷 / 01期

关键词：

Tandem reactions; Sulfa-Michael reactions; Sulfur heterocycles; Tetrahydrothiophenes; MEDICINE SALACIA-RETICULATA; ALPHA-GLUCOSIDASE INHIBITOR; CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; BIOLOGICAL-ACTIVITIES; REACTION METHODOLOGY; POTENT; DERIVATIVES; CONVENIENT; ESTERS;

D O I：

10.1016/j.tet.2011.10.064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

'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. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：208 / 213

页数：6

共 32 条

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