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
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
  • [21] HIGHLY ASYMMETRIC PUMMERER-TYPE CYCLIZATION OF CHIRAL, NON-RACEMIC BETA-AMIDO SULFOXIDES
    KITA, Y
    SHIBATA, N
    KAWANO, N
    TOHJO, T
    FUJIMORI, C
    MATSUMOTO, K
    FUJITA, S
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (19): : 2405 - 2410
  • [22] MECHANISTIC STUDIES OF A PUMMERER-TYPE REACTION IN ACYCLIC AND RIGID CYCLIC SULFOXIDES INDUCED BY KETENE TERT-BUTYLDIMETHYLSILYL METHYL ACETAL
    KITA, Y
    SHIBATA, N
    YOSHIDA, N
    KAWANO, N
    FUJIMORI, C
    YOSHIKAWA, N
    FUJITA, S
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (22): : 2829 - 2834
  • [23] CHEMISTRY OF O-SILYLATED KETENE ACETALS - AN EFFICIENT SYNTHESIS OF CARBAPENEM AND 1-BETA-METHYLCARBAPENEM INTERMEDIATES
    KITA, Y
    SHIBATA, N
    TOHJO, T
    YOSHIDA, N
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (14): : 1795 - 1799
  • [24] CHEMISTRY OF O-SILYLATED KETENE ACETALS - STEREOCONTROLLED SYNTHESIS OF 3-BENZOYLAMINO-2,3-DIDEOXYPENTOSES BY A 1,3-ADDITION TO CHIRAL NITRONES
    KITA, Y
    TAMURA, O
    ITOH, F
    KISHINO, H
    MIKI, T
    KOHNO, M
    TAMURA, Y
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1989, 37 (08) : 2002 - 2007
  • [25] CHEMISTRY OF O-SILYLATED KETENE ACETALS - PREPARATION OF ALPHA-SILOXY PHENYL SULFIDES AND METHYL 3-(PHENYLTHIO)BUTYRATES FROM ALKYL PHENYL SULFOXIDES
    KITA, Y
    TAMURA, O
    YASUDA, H
    ITOH, F
    TAMURA, Y
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1985, 33 (10) : 4235 - 4241
  • [26] MICHAEL TYPE REACTION OF O-SILYLATED KETENE ACETALS WITH ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS PROMOTED BY TITANIUM TETRACHLORIDE
    SAIGO, K
    OSAKI, M
    MUKAIYAMA, T
    CHEMISTRY LETTERS, 1976, (02) : 163 - 164