HOMOCHIRAL 1-METHOXY-3-SULFINYL-1,3-BUTADIENES DERIVED FROM 10-MERCAPTOISOBORNEOL

被引:38
作者
AVERSA, MC [1 ]
BONACCORSI, P [1 ]
GIANNETTO, P [1 ]
JAFARI, SMA [1 ]
JONES, DN [1 ]
机构
[1] UNIV SHEFFIELD,DEPT CHEM,SHEFFIELD S3 7HF,S YORKSHIRE,ENGLAND
关键词
D O I
10.1016/S0957-4166(00)80505-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Simple syntheses of homochiral (Z)- and (E)-1-methoxy-3-alkylsulfinyl-1,3-butadienes were provided by the cycloaddition of (IS)-d-isobornyl-10-sulfenic acid to (Z)- and (E)-1-methoxybut-1-en-3-yne. Asymmetric induction pertained for such cycloadditions, which also provided homochiral dienes from 1-ethynylcyclohex-1-ene.
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收藏
页码:701 / 704
页数:4
相关论文
共 18 条
[1]   HIGHLY DIASTEREOSELECTIVE DIELS-ALDER REACTION OF OPTICALLY-ACTIVE 2-PARA-TOLYLSULPHINYL-2-CYCLOALKENONES WITH CYCLOPENTADIENE [J].
ALONSO, I ;
CARRETERO, JC ;
RUANO, JLG .
TETRAHEDRON LETTERS, 1989, 30 (29) :3853-3856
[2]  
ARAI Y, 1986, SYNTHETIC COMMUN, V16, P233
[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 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
[5]   1ST SYNTHESES OF CHIRAL 2-SULFINYLBUTADIENES [J].
BONFAND, E ;
GOSSELIN, P ;
MAIGNAN, C .
TETRAHEDRON LETTERS, 1992, 33 (17) :2347-2348
[6]   SYNTHESIS AND ASYMMETRIC DIELS-ALDER REACTIONS OF (S)-2-PARA-TOLYLSULFINYL-1,4-BENZOQUINONE [J].
CARRENO, MC ;
RUANO, JLG ;
URBANO, A .
TETRAHEDRON LETTERS, 1989, 30 (30) :4003-4006
[7]   SELF-INDUCED DIASTEREOSELECTIVE OXIDATION OF VINYL SULFIDES BEARING A CHIRAL HYDROXY GROUP AS A WAY OF PREPARATION OF OPTICALLY-ACTIVE SULFINYL DIENOPHILES AND THEIR USE IN THE ASYMMETRIC DIELS-ALDER REACTION TO CYCLOPENTADIENE [J].
DELUCCHI, O ;
LUCCHINI, V ;
MARCHIORO, C ;
VALLE, G ;
MODENA, G .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (09) :1457-1466
[8]  
FURUKAWA N, 1988, CHEM SULPHONES SULPH, P541
[9]   HIGHLY DIASTEREOSELECTIVE OXIDATIONS OF A THIOETHER APPENDED WITH A NEIGHBORING HYDROXYL GROUP [J].
GLASS, RS ;
SETZER, WN ;
PRABHU, UDG ;
WILSON, GS .
TETRAHEDRON LETTERS, 1982, 23 (23) :2335-2338
[10]   STEREOSELECTIVE SYNTHESIS OF ALCOHOLS .2. STEREOCHEMISTRY OF THE [2,3]SIGMATROPIC REARRANGEMENT OF 3-SUBSTITUTED 2-ALKENYL SULFOXIDES [J].
GOLDMANN, S ;
HOFFMANN, RW ;
MAAK, N ;
GEUEKE, KJ .
CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (03) :831-844