HIGHLY REGIOSELECTIVE AND STEREOSELECTIVE PREPARATION OF Z-SILYL ENOL ETHERS AND Z-ENOL ESTERS FROM KETONES VIA MANGANESE ENOLATES

被引:19
|
作者
CAHIEZ, G
FIGADERE, B
CLERY, P
机构
[1] Laboratoire de Chimie des Organoéléments, associé au CNRS Université P. et M. Curie, F-75252 Paris Cédex 05
关键词
D O I
10.1016/S0040-4039(00)73415-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Mn-enolates are easily and quantitatively obtained under mild conditions (THF, -10 degrees C to rt, 1h) by treatment of ketones with aromatic Mn-amides such as Ph(Me)NMnZ. They allow to prepare Z silyl enol ethers and Z enol esters in high yields and with an excellent regio- and stereoselectivity (kinetic product: greater than or equal to 99%, Z/E: 93/7 to 100/0).
引用
收藏
页码:6295 / 6298
页数:4
相关论文
共 50 条
  • [31] AN EFFICIENT AND CONVENIENT METHOD FOR THE PREPARATION OF ALPHA-METHYLENATED KETONES FROM SILYL ENOL ETHERS
    HAYASHI, M
    MUKAIYAMA, T
    CHEMISTRY LETTERS, 1987, (07) : 1283 - 1286
  • [32] HIGHLY REGIOSELECTIVE MONOALKYLATION OF KETONES VIA MANGANESE ENOLATES PREPARED FROM MANGANESE AMIDES
    CAHIEZ, G
    FIGADERE, B
    CLERY, P
    TETRAHEDRON LETTERS, 1994, 35 (19) : 3065 - 3068
  • [33] REGIOSELECTIVE PREPARATION OF ALPHA,BETA-UNSATURATED KETONES VIA THE DIRECT DEHYDROGENATION OF TRIISOPROPYLSILYL ENOL ETHERS
    EVANS, PA
    LONGMIRE, JM
    MODI, DP
    TETRAHEDRON LETTERS, 1995, 36 (23) : 3985 - 3988
  • [34] Intramolecular [1,4]-S- to O-Silyl Migration: A Useful Strategy for Synthesizing Z-Silyl Enol Ethers with Diverse Thioether Linkages
    Sun, Changzhen
    Zhang, Yuebao
    Xiao, Peihong
    Li, Hongze
    Sun, Xianwei
    Song, Zhenlei
    ORGANIC LETTERS, 2014, 16 (03) : 984 - 987
  • [35] Regio- and stereoselective preparation of (Z)-silyl enol ethers by three-component coupling using α,β-unsaturated acylsilanes as core building blocks
    Tsubouchi, Akira
    Sasaki, Natsuki
    Enatsu, Shouko
    Takeda, Takeshi
    TETRAHEDRON LETTERS, 2013, 54 (10) : 1264 - 1267
  • [36] BORON ENOLATES IN STEREOSELECTIVE SYNTHESES OF 2-ENITOLS FROM O-BENZYL ALDOSES BY REACTION WITH BOROHYDRIDE IN 2-PROPANOL - CONFIGURATION OF E-ENOL AND Z-ENOL FROM PROTON RELAXATION RATES
    RAO, VS
    PERLIN, AS
    JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (17): : 3265 - 3269
  • [37] REGIOSPECIFIC PROCEDURE FOR THE PREPARATION OF SILYL ENOL ETHERS FROM ALPHA-(N-ALKOXYCARBONYLAMINO)KETONES
    ROSSI, L
    PECUNIOSO, A
    TETRAHEDRON LETTERS, 1994, 35 (29) : 5285 - 5288
  • [38] Addition of TMS-Substituted Oxiranyl Anions to Acylilanes. A Highly Stereoselective Approach to Tetrasubstitued (Z)-β-Hydroxy-α-TMS Silyl Enol Ethers
    Song, Zhenlei
    Kui, Leizhou
    Sun, Xianwei
    Li, Linjie
    ORGANIC LETTERS, 2011, 13 (06) : 1440 - 1443
  • [39] PREPARATION OF CYCLOPROPANOLS FROM ALDEHYDES AND KETONES VIA TRIMETHYLSILYL ENOL ETHERS AND TRIMETHYLSILOXYCYCLOPROPANE DERIVATIVES
    GIRARD, C
    CONIA, JM
    JOURNAL OF CHEMICAL RESEARCH-S, 1978, (05): : 182 - 183
  • [40] ENANTIOSELECTIVE ACYLATION OF ENOLATES - THE REACTION OF (4R)-TRANS-DIETHYL 2-ALKYL-2-METHOXY-1,3-DIOXOLANE-4,5-DICARBOXYLATES WITH E-SILYL AND Z-SILYL ENOL ETHERS
    BASILE, T
    LONGOBARDO, L
    TAGLIAVINI, E
    TROMBINI, C
    UMANIRONCHI, A
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (06) : 391 - 392