Unexpected conversion of vinyl sulfoxides into carbonyl compounds by means of iodotrimethylsilane

被引:7
作者
Aversa, MC
Barattucci, A
Bonaccorsi, P
Bruno, G
Giannetto, P
Policicchio, M
机构
[1] Univ Messina, Dipartimento Chim Organ & Biol, I-98166 Messina, Italy
[2] Univ Messina, Dipartimento Chim Inorgan, I-98166 Messina, Italy
关键词
carbonyl compounds; desulfurization; iodotrimethylsilane; sulfoxides;
D O I
10.1016/S0040-4039(00)00612-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The unexpected and previously unknown TMSI-promoted conversion of cl,P-unsaturated sulfoxides into carbonyl compounds and disulfides is described. It occurs in good yields under mild conditions. The examples provided support the generality and efficiency of this procedure which acts as a good method for removing the sulfinyl group with the advantage of transforming-the vinyl sulfoxides into carbonyl compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4441 / 4445
页数:5
相关论文
共 19 条
[1]   ASYMMETRIC DIELS-ALDER REACTION OF OPTICALLY-ACTIVE ALPHA-(2-EXO-HYDROXY-10-BORNYL)SULFINYLMALEIMIDES AND ITS APPLICATION TO OPTICALLY-ACTIVE 5-FUNCTIONALIZED PYRROLINES VIA RETRO-DIELS-ALDER REACTION [J].
ARAI, Y ;
MATSUI, M ;
FUJII, A ;
KONTANI, T ;
OHNO, T ;
KOIZUMI, T ;
SHIRO, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (01) :25-39
[2]   AN ENANTIODIVERGENT SYNTHESIS OF FUSED BICYCLO[2.2.1]HEPTANE LACTONES VIA AN ASYMMETRIC DIELS-ALDER REACTION [J].
ARAI, Y ;
MATSUI, M ;
KOIZUMI, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (04) :1233-1234
[3]   SYNTHESIS AND ASYMMETRIC DIELS-ALDER REACTION OF DIMETHYL (D-ISOBORNEOL-10-SULPHINYL)MALEATE - NOVEL ROUTE TO KEY INTERMEDIATES FOR SYNTHESIS OF SOME CARBOCYCLIC NUCLEOSIDES AND TERPENOIDS [J].
ARAI, Y ;
HAYASHI, K ;
MATSUI, M ;
KOIZUMI, T ;
SHIRO, M ;
KURIYAMA, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (07) :1709-1716
[4]   Synthesis and asymmetric Diels-Alder reactions of enantiopure 3-(alkylsulfinyl)-1-methoxy-1,3-butadienes [J].
Aversa, MC ;
Barattucci, A ;
Bonaccorsi, P ;
Giannetto, P ;
JOnes, DN .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (13) :4376-4384
[5]   Diels-Alder reactions of (Rs)-3-[(1S)-isoborneol-10-sulfinyl]-1-methoxybuta-1,3-dienes with electron-deficient carbodienophiles.: The effects of Lewis acid catalysis [J].
Aversa, MC ;
Barattucci, A ;
Bonaccorsi, P ;
Giannetto, P ;
Panzalorto, M ;
Rizzo, S .
TETRAHEDRON-ASYMMETRY, 1998, 9 (09) :1577-1587
[6]   Diels-Alder reactions of enantiopure [(1S)-isoborneol-10-sulfinyl]- and [(1S-exo)-2-bornylsulfinyl]vinylcyclohexenes with maleimides [J].
Aversa, MC ;
Barattucci, A ;
Bonaccorsi, P ;
Giannetto, P ;
Nicolò, F ;
Rizzo, S .
TETRAHEDRON-ASYMMETRY, 1999, 10 (20) :3907-3917
[7]   NEW DESULFURIZATIONS BY NICKEL-CONTAINING COMPLEX REDUCING AGENTS [J].
BECKER, S ;
FORT, Y ;
CAUBERE, P .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) :6194-6198
[8]   SYNTHESIS OF ALKENYL SULFOXIDES BY INTRAMOLECULAR AND INTERMOLECULAR ADDITION OF SULFENIC ACIDS TO ALKYNES [J].
BELL, R ;
COTTAM, PD ;
DAVIES, J ;
JONES, DN .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (07) :2106-2115
[9]   APPLICATIONS OF SULFOXIDES TO ASYMMETRIC-SYNTHESIS OF BIOLOGICALLY-ACTIVE COMPOUNDS [J].
CARRENO, MC .
CHEMICAL REVIEWS, 1995, 95 (06) :1717-1760
[10]   A NEW RESOLUTION PROCEDURE FOR THE PREPARATION OF BOTH (R)-(+)-4-TERT-BUTOXYCYCLOPENT-2-ENONE AND (S)-(-)-4-TERT-BUTOXYCYCLOPENT-2-ENONE FROM RACEMIC 4-TERT-BUTOXYCYCLOPENT-2-ENONE AND CONVERSION OF (R)-(+)-4-TERT-BUTOXYCYCLOPENT-2-ENONE INTO (R)-(+)-4-ACETOXYCYCLOPENT-2-ENONE - A NEW METHOD FOR THE DETERMINATION OF THE ENANTIOMERIC PURITIES OF THE RESOLVED ENONES [J].
ESCHLER, BM ;
HAYNES, RK ;
IRONSIDE, MD ;
KREMMYDAS, S ;
RIDLEY, DD ;
HAMBLEY, TW .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (15) :4760-4766