REACTIONS OF CHIRAL 2-PARA-TOLYSULFINYLCYCLOALKANONES WITH ALME3

被引:18
作者
BUENO, AB
CARRENO, MC
FISCHER, J
RUANO, JLG
PENA, B
PENAS, L
RUBIO, A
机构
[1] UNIV AUTONOMA MADRID, DEPT QUIM, CANTOBLANCO, E-28049 MADRID, SPAIN
[2] UNIV STRASBOURG 1, CRISTALLOCHIM LAB, UA 424, F-67070 STRASBOURG, FRANCE
关键词
D O I
10.1016/S0040-4039(00)79719-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reactions of (S2,Rs) and (R2,Rs)-2-p-tolylsulfinylcyclohexanones with AlMe3/ZnCl2 only yield the cyclohexylmethylcarbinols with R configuration at hydroxylic carbon. The (R1,S2,Rs)-1-methyl-2-p-tolylsulfinylcyclopentanol was the only compound obtained in the reaction of Me3Al with both epimeric 2-p-tolylsulfinylcyclopentanones. The d.e. of both reactions are higher than 96%.
引用
收藏
页码:3191 / 3194
页数:4
相关论文
共 5 条
  • [1] SYNTHESIS AND REDUCTION OF CHIRAL SULFINYL CYCLOHEXANONES
    CARRENO, MC
    RUANO, JLG
    RUBIO, A
    [J]. TETRAHEDRON LETTERS, 1987, 28 (41) : 4861 - 4864
  • [2] STEREOSELECTIVE REDUCTIONS OF 2-KETO SULFOXIDES WITH HYDRIDES
    CARRENO, MC
    RUANO, JLG
    MARTIN, AM
    PEDREGAL, C
    RODRIGUEZ, JH
    RUBIO, A
    SANCHEZ, J
    SOLLADIE, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) : 2120 - 2128
  • [3] SYNTHESIS OF CHIRAL CYCLIC ALPHA-PARA-TOLYLSULFINYL KETONES
    CARRENO, MC
    RUANO, JLG
    PEDREGAL, C
    RUBIO, A
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (07): : 1335 - 1337
  • [4] FRENZ BA, 1978, ENRAF NONIUS CAD4 SD, P64
  • [5] DIASTEREOFACIAL CONTROL IN THE REACTION OF (R)-ALPHA-PARA-TOLYLSULFINYL) ACETOPHENONES WITH SEVERAL ORGANOMETALLICS
    FUJISAWA, T
    FUJIMURA, A
    UKAJI, Y
    [J]. CHEMISTRY LETTERS, 1988, (09) : 1541 - 1544