Efficient α-alkylation and silylation of aromatic O-tert-butyldimethylsilyl ketoximes

被引:5
|
作者
Ortiz-Marciales, M [1 ]
De Jesús, M [1 ]
Quiñones, L [1 ]
Figueroa, D [1 ]
Montes, YL [1 ]
Burgos, C [1 ]
Moctezuma, B [1 ]
机构
[1] Univ Puerto Rico, Dept Chem, Humacao Coll, CUH Stn, Humacao, PR 00791 USA
关键词
alkylation; alkyl halide; benzylation; oxime; silicon and compounds; silicon halides;
D O I
10.1016/S0040-4020(99)00731-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The a-alkylation and silylation of para substituted acetophenones, 1- and 2-indanone (O-TBS) oximes at various reaction conditions, were studied. Optimum conversions from 82% to 100% were afforded for the alkylation and silylation of these (O-TBS) ketoximes with LDA at -78 degrees C, using electrophiles, such as, methyl iodide, ethylbromide, benzyl bromide and trimethylchlorosilane. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:12275 / 12286
页数:12
相关论文
共 50 条
  • [41] Confirmation of the structure of tetra-O-(tert-butyldimethylsilyl)-D-glucono-1,4-lactone formed by silylation of D-glucono-1,5-lactone
    Singh, J
    DiMarco, J
    Kissick, TP
    Deshpande, P
    Gougoutas, JZ
    [J]. CARBOHYDRATE RESEARCH, 2002, 337 (06) : 563 - 564
  • [42] Synthesis of heptakis (2, 3-di-o-methyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin
    Xiong, YT
    Hao, JS
    Pan, JG
    Guo, W
    [J]. PROGRESS OF FINE CHEMISTRY AND FUNCTIONAL POLYMERS, 1998, : 135 - 136
  • [43] Phosphorylated derivatives on the basis of per-6-O-(tert-butyldimethylsilyl)cyclodextrins
    Grachev, MK
    Kurochkina, GI
    Mishina, VY
    Mustafin, IG
    Nifant'ev, EE
    [J]. RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 1999, 69 (11) : 1702 - 1707
  • [44] Steric and electronic effects on the reduction of O-silylated aromatic ketoximes with borane
    Ortiz-Marciales, M
    Figueroa, D
    López, JA
    De Jesús, M
    Vega, R
    [J]. TETRAHEDRON LETTERS, 2000, 41 (34) : 6567 - 6570
  • [45] ALKYL EXCHANGE-REACTIONS IN TRIFLUOROACETIC ACID - TERT-BUTYL TRIFLUOROACETATE, AND EFFICIENT ALKYLATION AGENT FOR AROMATIC-COMPOUNDS
    SVANHOLM, U
    PARKER, VD
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (06): : 562 - 566
  • [46] Alkylation of aromatic amines by tert-enamides: Direct access to protected aminals
    Halimehjani, Azim Ziyaei
    Goudarzi, Mehri
    Nosood, Yazdanbakhsh Lotfi
    [J]. SYNTHETIC COMMUNICATIONS, 2017, 47 (21) : 2022 - 2029
  • [47] Analysis of heterocyclic aromatic amines in foods by gas chromatography-mass spectrometry as their tert.-butyldimethylsilyl derivatives
    Casal, S
    Mendes, E
    Fernandes, JO
    Oliveira, MBPP
    Ferreira, MA
    [J]. JOURNAL OF CHROMATOGRAPHY A, 2004, 1040 (01) : 105 - 114
  • [48] Stereoselective α-alkylation of methyl 6-deoxy-3,4-di-O-(tert-butyldimethylsilyl)-2-O-(2-methyl-3-oxobutanoyl)-α-D-glucopyranoside
    Akashi, Yoko
    Takao, Ken-ichi
    Tadano, Kin-ichi
    [J]. TETRAHEDRON LETTERS, 2009, 50 (10) : 1139 - 1142
  • [49] Site selectivity in the alpha-silyl lithiation of 3,4,6-tris-O-(tert-butyldimethylsilyl)-D and 3,4-bis-O-(tert-butyldimethylsilyl)-6-deoxy-L-glucal with tert-butyllithium
    Friesen, RW
    Trimble, LA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03): : 1165 - 1168
  • [50] ORGANIC PEROXIDES, .12. PREPARATION AND THERMOLYSIS OF O-(TERT-BUTYLPEROXYCARBONYL)KETOXIMES
    RUCHARDT, C
    PANTKE, R
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1971, 104 (11): : 3456 - &