THE 1ST HIGHLY ASYMMETRIC PUMMERER-TYPE REACTION IN CHIRAL ACYCLIC SULFOXIDES - CHEMISTRY OF O-SILYLATED KETENE ACETALS

被引：28
|
作者：
KITA, Y
SHIBATA, N
YOSHIDA, N
机构：
[1] Faculty of Pharmaceutical Sciences, Osaka University 1-6, Suita, Osaka, 565, Yamada-oka
来源：
TETRAHEDRON LETTERS | 1993年 / 34卷 / 25期
关键词：
PUMMERER REACTION; O-SILYLATED KETENE ACETALS; CHIRAL SULFOXIDES; ACYCLIC; ASYMMETRIC;
D O I：
10.1016/S0040-4039(00)60616-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The chiral sulfoxides (4) were reacted with O-silylated ketene acetal (2) in acetonitrile to give the corresponding alpha-siloxysulfides (5) in high degree of stereochemistry and high yields.
引用
收藏
页码：4063 / 4066
页数：4
相关论文
共 26 条
  • [1] Asymmetric pummerer-type reaction induced by O-silylated ketene acetals
    Kita, Yasuyuki
    Shibata, Norio
    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 1994, 52 (09):
  • [2] ASYMMETRIC PUMMERER-TYPE REACTION INDUCED BY O-SILYLATED KETENE ACETALS
    KITA, Y
    SHIBATA, N
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1994, 52 (09) : 746 - 753
  • [3] FIRST HIGHLY ASYMMETRIC PUMMERER-TYPE REACTION IN CHIRAL, NON-RACEMIC ACYCLIC SULFOXIDES INDUCED BY O-SILYLATED KETENE ACETAL
    KITA, Y
    SHIBATA, N
    YOSHIDA, N
    FUJITA, S
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (22): : 3335 - 3341
  • [4] Asymmetric pummerer-type reactions induced by O-silylated ketene acetals
    Kita, Y
    Shibata, N
    SYNLETT, 1996, (04) : 289 - 296
  • [5] MECHANISTIC STUDIES OF PUMMERER REACTION IN ACYCLIC SULFOXIDES INDUCED BY O-SILYLATED KETENE ACETALS
    KITA, Y
    SHIBATA, N
    YOSHIDA, N
    FUKUI, S
    FUJIMORI, C
    TETRAHEDRON LETTERS, 1994, 35 (16) : 2569 - 2572
  • [6] Mechanistic studies of a Pummerer-type reaction in acyclic and rigid cyclic sulfoxides induced by O-silylated ketene acetal
    J Chem Soc Perkin Trans 1, (2829):
  • [7] A HIGHLY ASYMMETRIC PUMMERER-TYPE CYCLIZATION OF CHIRAL, NON-RACEMIC BETA-AMIDOSULFOXIDES INDUCED BY O-SILYLATED KETENE ACETALS
    KITA, Y
    SHIBATA, N
    KAWANO, N
    TOHJO, T
    FUJIMORI, C
    MATSUMOTO, K
    TETRAHEDRON LETTERS, 1995, 36 (01) : 115 - 118
  • [8] Enantioselective Pummerer-type rearrangement by reaction of O-silylated ketene acetal with enantiopure a-substituted sulfoxides
    J Chem Soc Perkin Trans 1, 12 (1763):
  • [9] Enantioselective additive pummerer-type reaction in chiral, non-racemic vinyl sulfoxides induced by O-silylated ketene acetal
    Shibata, N
    Fujimori, C
    Fujita, S
    Kita, Y
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1996, 44 (05) : 892 - 894
  • [10] Enantioselective Pummerer-type rearrangement by reaction of O-silylated ketene acetal with enantiopure alpha-substituted sulfoxides
    Kita, Y
    Shibata, N
    Fukui, S
    Bando, M
    Fujita, S
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (12): : 1763 - 1767
123