Remarkable effect of lithium bromide in the enantioselective protonation with α-sulfinyl alcohols

被引:25
作者
Asensio, G [1 ]
Aleman, PA [1 ]
Domingo, LR [1 ]
Medio-Simón, M [1 ]
机构
[1] Univ Valencia, Dept Quim Organ, E-46100 Burjassot, Spain
关键词
D O I
10.1016/S0040-4039(98)00469-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The favourable effect of lithium bromide enhancing the facial enantioselectivity in the protonation of methyl tetralone enolate with alpha-sulfinyl alcohols is described. Theoretical calculations allow to propose a model to explain the stereochemical course of the protonation reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3277 / 3280
页数:4
相关论文
共 21 条
  • [1] BRAVO P, 1988, SYNTHESIS-STUTTGART, P955
  • [2] A NEW PRACTICAL SYNTHESIS OF SILYL ENOL ETHERS .1. FROM SIMPLE ALDEHYDES AND KETONES
    CAZEAU, P
    DUBOUDIN, F
    MOULINES, F
    BABOT, O
    DUNOGUES, J
    [J]. TETRAHEDRON, 1987, 43 (09) : 2075 - 2088
  • [3] Theoretical model of solvated lithium dienediolates of methyl substituted 2-butenoic acids
    Domingo, LR
    Gil, S
    Mestres, R
    Picher, MT
    [J]. TETRAHEDRON, 1996, 52 (33) : 11105 - 11112
  • [4] THEORETICAL-MODEL OF SOLVATED LITHIUM DIENEDIOLATE OF 2-BUTENOIC ACID
    DOMINGO, LR
    GIL, S
    MESTRES, R
    PICHER, MT
    [J]. TETRAHEDRON, 1995, 51 (26) : 7207 - 7214
  • [5] Fehr C., 1996, Angew. Chem., V35, P2566
  • [6] HYDROCHLORIDE OF CHIRAL PIPERAZINE AS A CHIRAL PROTON SOURCE
    FUJI, K
    TANAKA, K
    MIYAMOTO, H
    [J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (02) : 247 - 259
  • [7] STEREOSELECTIVE PROTONATION OF CARBANIONS .5. EFFECTS OF REACTION CONDITIONS ON THE ENANTIOSELECTIVE PROTONATION OF LACTONE ENOLATES
    GERLACH, U
    HAUBENREICH, T
    HUNIG, S
    [J]. CHEMISCHE BERICHTE, 1994, 127 (10) : 1981 - 1988
  • [8] First example of a highly enantioselective catalytic protonation of silyl enol ethers using a novel Lewis acid-assisted Bronsted acid system
    Ishihara, K
    Nakamura, S
    Kaneeda, M
    Yamamoto, H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (50) : 12854 - 12855
  • [9] BETA-HYDROXY SULFOXIDE DERIVATIVES AS A POWERFUL CHIRAL PROTONATING REAGENT
    KOSUGI, H
    HOSHINO, K
    UDA, H
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1994, 95-6 (1-4): : 401 - 402
  • [10] Highly enantiofacial protonation of prochiral lithium enolates with chiral beta-hydroxy sulfoxides
    Kosugi, H
    Hoshino, K
    Uda, H
    [J]. TETRAHEDRON LETTERS, 1997, 38 (39) : 6861 - 6864