HIGHLY REGIOSELECTIVE MONOALKYLATION OF KETONES VIA MANGANESE ENOLATES PREPARED FROM MANGANESE AMIDES

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)76829-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ketones are regioselectively converted to Mn-enolates by treatment with Mn-amides such as Ph(Me)NMnCl in THF at 20 degrees C. Mn-enolates can then be regioselectively monoalkylated in good yields. The formation of di or polyalkylated products is never observed (< 1%).
引用
收藏
页码:3065 / 3068
页数:4
相关论文
共 50 条
  • [1] HIGHLY REGIOSELECTIVE MONOALKYLATION OF KETONES VIA MANGANESE ENOLATES PREPARED FROM LITHIUM ENOLATES
    CAHIEZ, G
    CHAU, K
    CLERY, P
    [J]. TETRAHEDRON LETTERS, 1994, 35 (19) : 3069 - 3072
  • [2] Regioselective monoalkylation of ketones via their manganese enolates: 2-benzyl-6-methylcyclohexanone from 2-methylcyclohexanone
    Cahiez, G
    Chau, F
    Blanchot, B
    [J]. ORGANIC SYNTHESES, VOL 76 - 1999, 1999, 76 : 239 - 251
  • [3] HIGHLY REGIOSELECTIVE AND STEREOSELECTIVE PREPARATION OF Z-SILYL ENOL ETHERS AND Z-ENOL ESTERS FROM KETONES VIA MANGANESE ENOLATES
    CAHIEZ, G
    FIGADERE, B
    CLERY, P
    [J]. TETRAHEDRON LETTERS, 1994, 35 (34) : 6295 - 6298
  • [4] ALPHA-METHYLATION OF KETONES VIA MANGANESE-ENOLATES - ABSENCE OF UNDESIRED POLYALKYLATION
    REETZ, MT
    HANING, H
    [J]. TETRAHEDRON LETTERS, 1993, 34 (46) : 7395 - 7398
  • [5] Synthesis of α-hydrazino ketones via regio- and stereoselective electrophilic amination of manganese enolates and enamines
    Dessole, G
    Bernardi, L
    Bonini, BF
    Capitò, E
    Fochi, M
    Herrera, RP
    Ricci, A
    Cahiez, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (24): : 8525 - 8528
  • [6] Manganese-Catalyzed α-Alkylation of Ketones, Esters, and Amides Using Alcohols
    Chakraborty, Subrata
    Daw, Prosenjit
    Ben David, Yehoshoa
    Milstein, David
    [J]. ACS CATALYSIS, 2018, 8 (11): : 10300 - 10305
  • [7] A Highly Active Manganese Precatalyst for the Hydrosilylation of Ketones and Esters
    Mukhopadhyay, Tufan K.
    Flores, Marco
    Groy, Thomas L.
    Trovitch, Ryan J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (03) : 882 - 885
  • [8] A Manganese Pre-Catalyst: Mild Reduction of Amides, Ketones, Aldehydes, and Esters
    Kelly, Colin M.
    McDonald, Robert
    Sydora, Orson L.
    Stradiotto, Mark
    Turculet, Laura
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (50) : 15901 - 15904
  • [9] Synthesis of α-Trifluoromethylated Ketones from α,β-Unsaturated Ketones via Catecholboron Enolates
    Keerthika, K.
    Bazil Muhammed, S.
    Geetharani, K.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (16): : 11480 - 11486
  • [10] Highly regioselective alkylation at the more hindered α-site of unsymmetrical ketones by use of their potassium enolates.: A comparative study with lithium enolates
    Quesnel, Y
    Bidois-Sery, L
    Poirier, JM
    Duhamel, L
    [J]. SYNLETT, 1998, (04) : 413 - +