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.
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收藏
页码：208 / 213
页数：6
相关论文
共 32 条
[1]   SIR97:: a new tool for crystal structure determination and refinement [J].
Altomare, A ;
Burla, MC ;
Camalli, M ;
Cascarano, GL ;
Giacovazzo, C ;
Guagliardi, A ;
Moliterni, AGG ;
Polidori, G ;
Spagna, R .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1999, 32 :115-119
[2]   A convenient and easy synthesis of γ-nitro-α-acetamido esters [J].
Ballini, R ;
Balsamini, C ;
Diamantini, G ;
Savoretti, N .
SYNTHESIS-STUTTGART, 2005, (07) :1055-1057
[3]   ENANTIOSELECTIVE SYNTHESIS OF (-)-MEROQUINENE THROUGH TANDEM MICHAEL REACTION METHODOLOGY [J].
BARCO, A ;
BENETTI, S ;
DERISI, C ;
POLLINI, GP ;
ROMAGNOLI, R ;
SPALLUTO, G ;
ZANIRATO, V .
TETRAHEDRON, 1994, 50 (08) :2583-2590
[4]   A NEW APPROACH TO KAINOIDS THROUGH TANDEM MICHAEL REACTION METHODOLOGY - APPLICATION TO THE ENANTIOSELECTIVE SYNTHESIS OF (+)-ALPHA-ALLOKAINIC AND (-)-ALPHA-ALLOKAINIC ACID AND TO THE FORMAL SYNTHESIS OF (-)-ALPHA-KAINIC ACID [J].
BARCO, A ;
BENETTI, S ;
SPALLUTO, G ;
CASOLARI, A ;
POLLINI, GP ;
ZANIRATO, V .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6279-6286
[5]   Convenient 'one-pot' synthesis of 3,4-substituted tetrahydrothiophenes through tandem Michael-Henry and Michael-Michael reactions [J].
Barco, Achille ;
Baricordi, Nikla ;
Benetti, Simonetta ;
De Risi, Carmela ;
Pollini, Gian Piero .
TETRAHEDRON LETTERS, 2006, 47 (46) :8087-8090
[6]  
Burnett M.N., 1996, ORTEP-III: Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations
[7]   Asymmetric 1,4 addition of Grignard reagents to chiral α,β-unsaturated esters in the presence of Lewis acids [J].
Cardillo, G ;
Gentilucci, L ;
Tolomelli, A ;
Tomasini, C .
TETRAHEDRON, 1999, 55 (19) :6231-6242
[8]   CHIRAL 2-ACETAMIDOACRYLATES IN CONJUGATE ADDITION ASYMMETRIC ENOLATE TRAPPING REACTIONS - ASYMMETRIC-SYNTHESIS OF PHENYLALANINE [J].
CATIVIELA, C ;
DIAZDEVILLEGAS, MD ;
GALVEZ, JA .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1992, 70 (09) :2325-2328
[9]   Convenient route to γ-nitro-α-amino acids:: conjugate addition of nitroalkanes to dehydroalanine derivatives [J].
Crossley, MJ ;
Fung, YM ;
Potter, JJ ;
Stamford, AW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (06) :1113-1121
[10]   Design of sulfides with a locked conformation as promoters of catalytic and asymmetric sulfonium ylide epoxidation [J].
Davoust, M ;
Brière, JF ;
Jaffrès, PA ;
Metzner, P .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :4166-4169
1234