Synthesis of pentafluorophenylmethylamines via silicon Mannich reaction

被引：27
作者：
Dilman, AD
Belyakov, PA
Korlyukov, AA
Struchkova, MI
Tartakovsky, VA
机构：
[1] ND Zelinskii Inst Organ Chem, Moscow 119991, Russia
[2] AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
来源：
ORGANIC LETTERS | 2005年 / 7卷 / 14期
关键词：
D O I：
10.1021/ol050845l
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The three-component coupling of aldehydes, secondary amines, and methoxytris(pentafluorophenyl)silane, MeOSi(C6F5)(3), affording pentafluorophenylmethylamines has been described. The generation of the five-coordinate silicate intermediate is believed to be the key feature responsible for the efficiency of the reaction.
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收藏
页码：2913 / 2915
页数：3
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共 24 条
  • [1] A convenient procedure for the preparation of α-aminoallenes using a three-component reaction of aldehyde, carbamate and propargylsilane
    Billet, M
    Schoenfelder, A
    Klotz, P
    Mann, A
    [J]. TETRAHEDRON LETTERS, 2002, 43 (08) : 1453 - 1456
  • [2] CHEN QY, 1990, J CHEM RES-S, P268
  • [3] REACTIVITY OF PENTACOORDINATE AND HEXACOORDINATE SILICON-COMPOUNDS AND THEIR ROLE AS REACTION INTERMEDIATES
    CHUIT, C
    CORRIU, RJP
    REYE, C
    YOUNG, JC
    [J]. CHEMICAL REVIEWS, 1993, 93 (04) : 1371 - 1448
  • [4] Carbon-carbon bond forming reactions mediated by silicon Lewis acids
    Dilman, AD
    Ioffe, SL
    [J]. CHEMICAL REVIEWS, 2003, 103 (03) : 733 - 772
  • [5] AROMATIC REACTIVITY .34. ACID CLEAVAGE OF (PENTAFLUOROPHENYL)-TRIMETHYL-STANNANE AND -SILANE
    EABORN, C
    TREVERTO.JA
    WALTON, DRM
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1967, 9 (02) : 259 - &
  • [6] Unexpected 1,2 syn diastereoselectivity in the three-component 'aza Sakurai-Hosomi' reaction
    Ella-Menye, JR
    Dobbs, W
    Billet, M
    Klotz, P
    Mann, A
    [J]. TETRAHEDRON LETTERS, 2005, 46 (11) : 1897 - 1900
  • [7] MECHANISM OF INACTIVATION OF ALANINE RACEMASE BY BETA,BETA,BETA-TRIFLUOROALANINE
    FARACI, WS
    WALSH, CT
    [J]. BIOCHEMISTRY, 1989, 28 (02) : 431 - 437
  • [8] First catalytic asymmetric synthesis of β-amino-β-polyfluoroalkyl ketones via proline-catalysed direct asymmetric carbon-carbon bond formation reaction of polyfluoroalkylated aldimines
    Funabiki, K
    Nagamori, M
    Goushi, S
    Matsui, M
    [J]. CHEMICAL COMMUNICATIONS, 2004, (17) : 1928 - 1929
  • [9] SYNTHETIC ASPECTS OF THE USE OF ORGANO-SILICON COMPOUNDS UNDER NUCLEOPHILIC CATALYSIS CONDITIONS
    FURIN, GG
    VYAZANKINA, OA
    GOSTEVSKY, BA
    VYAZANKIN, NS
    [J]. TETRAHEDRON, 1988, 44 (10) : 2675 - 2749
  • [10] Contribution of fluorine to protein-ligand affinity in the binding of fluoroaromatic inhibitors to carbonic anhydrase II
    Kim, CY
    Chang, JS
    Doyon, JB
    Baird, TT
    Fierke, CA
    Jain, A
    Christianson, DW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (49) : 12125 - 12134
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