STEREOCONTROLLED SYNTHESIS OF ENANTIOMERICALLY PURE 2-DIENYL SULFOXIDES VIA PALLADIUM-CATALYZED COUPLING REACTIONS

被引:44
作者
PALEY, RS [1 ]
WEERS, HL [1 ]
FERNANDEZ, P [1 ]
DELAPRADILLA, RF [1 ]
CASTRO, S [1 ]
机构
[1] CSIC,INST QUIM ORGAN,E-28006 MADRID,SPAIN
关键词
D O I
10.1016/0040-4039(95)00604-B
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantiopure 2-sulfinyl dienes can be prepared via regio- and stereoselective hydrostannylation of alkynylsulfoxides; after conversion to the corresponding vinyliodides these substrates may be coupled with vinylstannanes via Stille methodology in the presence of BHT.
引用
收藏
页码:3605 / 3608
页数:4
相关论文
共 18 条
[1]   AN EASY SYNTHESIS OF CHIRAL SULFINYL ALLYLIC BROMIDES AND THEIR USE IN THE PREPARATION OF (R)S-2-P-TOLYLSULFINYL-1,3-ALKADIENES AND (S)S-2-P-TOLYLSULFINYL-1,3-ALKADIENES [J].
BONFAND, E ;
GOSSELIN, P ;
MAIGNAN, C .
TETRAHEDRON-ASYMMETRY, 1993, 4 (07) :1667-1676
[2]   1ST SYNTHESES OF CHIRAL 2-SULFINYLBUTADIENES [J].
BONFAND, E ;
GOSSELIN, P ;
MAIGNAN, C .
TETRAHEDRON LETTERS, 1992, 33 (17) :2347-2348
[3]   OPTICALLY-ACTIVE SULFOXIDES BY ENANTIOSPECIFIC REACTIONS OF BROMOVINYL ARYL SULFOXIDES WITH GRIGNARD-REAGENTS [J].
CARDELLICCHIO, C ;
FIANDANESE, V ;
NASO, F ;
SCILIMATI, A .
TETRAHEDRON LETTERS, 1992, 33 (35) :5121-5124
[4]   LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS [J].
FARINA, V ;
KRISHNAN, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9585-9595
[5]   TRANSITION-METAL-CATALYZED ASYMMETRIC VINYLCYCLOPROPANE-CYCLOPENTENE REARRANGEMENTS - ASYMMETRIC-SYNTHESIS OF CYCLOPENTANE DERIVATIVES USING CHIRAL SULFOXIDES AS CHIRAL SOURCES [J].
HIROI, K ;
ARINAGA, Y .
TETRAHEDRON LETTERS, 1994, 35 (01) :153-156
[6]   SIMPLE AND STEREOCONTROLLED PREPARATION OF OPTICALLY PURE (E)-1-ALKENYL PARA-TOLYL AND (Z)-1-ALKENYL PARA-TOLYL SULFOXIDES VIA 1-ALKYNYL PARA-TOLYL SULFOXIDES [J].
KOSUGI, H ;
KITAOKA, M ;
TAGAMI, K ;
TAKAHASHI, A ;
UDA, H .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (06) :1078-1082
[7]   STUDIES IN GROUP 4 ORGANOMETALLIC CHEMISTRY .25. NUCLEOPHILIC TRANS-ADDITION OF ORGANOTIN HYDRIDES TO CARBON-CARBON TRIPLE BONDS [J].
LEUSINK, AJ ;
BUDDING, HA ;
DRENTH, W .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1967, 9 (02) :295-&
[8]   A HIGHLY SELECTIVE SYNTHESIS OF VERSATILE (E)-1-PHENYLTHIO VINYLSTANNANES [J].
MAGRIOTIS, PA ;
BROWN, JT ;
SCOTT, ME .
TETRAHEDRON LETTERS, 1991, 32 (38) :5047-5050
[9]  
MITCHELL TN, 1992, SYNTHESIS-STUTTGART, P803
[10]   STEREOCONTROLLED SYNTHESIS OF ENANTIOMERICALLY PURE DIENYL SULFOXIDES VIA PALLADIUM-CATALYZED COUPLING REACTIONS [J].
PALEY, RS ;
DEDIOS, A ;
DELAPRADILLA, RF .
TETRAHEDRON LETTERS, 1993, 34 (15) :2429-2432