AN IMPROVED REACTION OF TRIS(METHYLTHIO)METHANE WITH EPOXIDES - APPLICATION TO THE EFFICIENT SYNTHESIS OF BETA-HYDROXY ESTERS

被引：8
|
作者：
ABOOD, NA
机构：
[1] Department of Chemistry, Searle Research and Development, Skokie, Illinois
来源：
SYNTHETIC COMMUNICATIONS | 1993年 / 23卷 / 06期
关键词：
D O I：
10.1080/00397919308009842
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Tris(methylthio)methyllithium reacts efficiently with epoxides in THF:HMPA (5:1) at low temperature to give beta-hydroxy orthotrithiocarboxylates which are converted to beta-hydroxy esters in high yield.
引用
收藏
页码：811 / 815
页数：5
相关论文
共 50 条
  • [1] ASYMMETRICAL SYNTHESIS OF BETA-HYDROXY ESTERS BY REFORMATSKY REACTION IN PRESENCE OF (-) SPARTEINE
    GUETTE, M
    CAPILLON, J
    GUETTE, JP
    TETRAHEDRON, 1973, 29 (22) : 3659 - 3667
  • [2] ENANTIOSELECTIVE SYNTHESIS OF BETA-HYDROXY ESTERS BY INDIUM-INDUCED REFORMATSKY REACTION
    JOHAR, PS
    ARAKI, S
    BUTSUGAN, Y
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (06): : 711 - 713
  • [3] Simple and efficient stereocontrol of radical allylations of beta-hydroxy esters
    Gerster, M
    Audergon, L
    Moufid, N
    Renaud, P
    TETRAHEDRON LETTERS, 1996, 37 (35) : 6335 - 6338
  • [4] REACTION OF BETA-HYDROXY ESTERS WITH VINYL-MAGNESIUM CHLORIDE
    SUGA, K
    WATANABE, S
    FUJITA, T
    YOSHIDA, K
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1976, 34 (09) : 661 - 665
  • [5] REFORMATSKY REACTION IN A CONTINUOUS-FLOW SYSTEM - IMPROVED PROCEDURE FOR PREPARATION OF BETA-HYDROXY ESTERS
    RUPPERT, JF
    WHITE, JD
    JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (02): : 269 - 270
  • [6] AN ASYMMETRIC-SYNTHESIS OF BETA-FORMYL BETA-HYDROXY ESTERS
    SAKITO, Y
    ASAMI, M
    MUKAIYAMA, T
    CHEMISTRY LETTERS, 1980, (04) : 455 - 458
  • [7] A GENERAL AND FACILE SYNTHESIS OF BETA-HYDROXY AND GAMMA-HYDROXY PHOSPHONATES FROM EPOXIDES
    LI, ZG
    RACHA, S
    DAN, L
    ELSUBBAGH, H
    ABUSHANAB, E
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21): : 5779 - 5783
  • [8] STEREOSELECTIVE SYNTHESIS OF BETA-HYDROXY SUBSTITUTED TRANS-ALKENES BY REACTION OF TRANS-ALKENYLTRIALKYLALUMINATES WITH EPOXIDES
    NEGISHI, EI
    BABA, S
    KING, AO
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (01) : 17 - 18
  • [9] REFORMATSKY REACTION AT ROOM TEMPERATURE AND IN PRESENCE OF TRIMETHYL BORATE - IMPROVED PROCEDURES FOR PREPARATION OF BETA-HYDROXY ESTERS
    RATHKE, MW
    LINDERT, A
    JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (11): : 3966 - &
  • [10] A NEW CLASS OF RECOVERABLE CHIRAL SULFOXIDE - APPLICATION TO THE ASYMMETRIC-SYNTHESIS OF BETA-HYDROXY ESTERS
    WILLS, M
    BUTLIN, RJ
    LINNEY, ID
    TETRAHEDRON LETTERS, 1992, 33 (37) : 5427 - 5430
12345