Addition of carbon nucleophiles to cyclic N-acyliminium ions in SDS/water

被引:20
作者
Camilo, NS [1 ]
Pilli, RA [1 ]
机构
[1] UNICAMP, Inst Quim, BR-13084971 Campinas, SP, Brazil
关键词
N-acyliminium ions; nucleophilic addition; micelles; SDS; water;
D O I
10.1016/j.tetlet.2004.02.009
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The acid-catalyzed addition of 1,3-dicarbonyl compounds and activated olefins (silyl enol ethers and ethyl vinyl ether) to N-Boc-2-methoxypyrrolidine (1a) and N-Boc-2-methoxypiperidine (1b) in SDS/water medium is described. Good yields of the corresponding 2-substituted N-Boc pyrrolidines were generally observed from la while moderate yields prevailed from 1b. (C) 2004 Published by Elsevier Ltd.
引用
收藏
页码:2821 / 2823
页数:3
相关论文
共 24 条
  • [1] Mannich-type reaction catalyzed by HBF4 in water:: Effect of the loading of surfactant
    Akiyama, T
    Itoh, J
    Fuchibe, K
    [J]. SYNLETT, 2002, (08) : 1269 - 1272
  • [2] Intrinsic gas-phase electrophilic reactivity of cyclic N-alkyl- and N-acyliminium ions
    D'Oca, MGM
    Moraes, LAB
    Pilli, RA
    Eberlin, MN
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (11) : 3854 - 3864
  • [3] Diastereoselection of the addition of silyloxyfurans to five-, six- and seven-membered N-acyliminium ions
    de Oliveira, MDF
    Santos, LS
    Pilli, RA
    [J]. TETRAHEDRON LETTERS, 2001, 42 (40) : 6995 - 6997
  • [4] Catalytic asymmetric aldol reactions in water using a chiral Lewis-acid-surfactant-combined catalyst
    Kobayashi, S
    Mori, Y
    Nagayama, S
    Manabe, K
    [J]. GREEN CHEMISTRY, 1999, 1 (04) : 175 - 177
  • [5] Development of novel Lewis acid catalysts for selective organic reactions in aqueous media
    Kobayashi, S
    Manabe, K
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (04) : 209 - 217
  • [6] Kobayashi S, 2001, J BRAZIL CHEM SOC, V12, P627
  • [7] Catalytic asymmetric Mukaiyama aldol reactions in aqueous media
    Kobayashi, S
    Nagayama, S
    Busujima, T
    [J]. TETRAHEDRON, 1999, 55 (29) : 8739 - 8746
  • [8] Sc(OTf)3-catalyzed three-component reactions of aldehydes, amines and allyltributylstannane in micellar systems.: Facile synthesis of homoallylic amines in water
    Kobayashi, S
    Busujima, T
    Nagayama, S
    [J]. CHEMICAL COMMUNICATIONS, 1998, (01) : 19 - 20
  • [9] Kobayashi S, 1999, SYNLETT, P545
  • [10] Lewis acid catalysis in micellar systems. Sc(OTf)(3)-catalyzed aqueous aldol reactions of silyl enol ethers with aldehydes in the presence of a surfactant
    Kobayashi, S
    Wakabayashi, T
    Nagayama, S
    Oyamada, H
    [J]. TETRAHEDRON LETTERS, 1997, 38 (26) : 4559 - 4562