Enantioselective spirocyclizations from tryptophanol-derived oxazolopiperidone lactams

被引：32
作者：
Amat, Mercedes [1 ]
Santos, Maria M. M.
Gomez, Antonia M.
Jokic, Danica
Molins, Elies
Bosch, Joan
机构：
[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain
[2] Univ Autonoma Barcelona, Inst Ciencia Mat Barcelona, CSIC, E-08193 Barcelona, Spain
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 15期
关键词：
D O I：
10.1021/ol0712327
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A straightforward synthetic route to enantiopure spiro[indole-3,3'-indolizidines] is reported. The key step is a Lewis acid promoted cyclization of a N-a-tosyltryptophanol-derived oxazolopiperidone lactam in the presence of Et3SiH.
引用
收藏
页码：2907 / 2910
页数：4
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共 49 条
  • [1] A highly stereoselective synthesis of the indolo[2,3-a]quinolizine ring system and application to natural product synthesis
    Allin, SM
    Thomas, CI
    Allard, JE
    Doyle, K
    Elsegood, MRJ
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (19) : 4179 - 4186
  • [2] A facile and highly stereoselective approach to a polycyclic isoindolinone ring system via an N-acyliminium ion cyclization reaction
    Allin, SM
    Northfield, CJ
    Page, MI
    Slawin, AMZ
    [J]. TETRAHEDRON LETTERS, 1998, 39 (27) : 4905 - 4908
  • [3] Alkylation of phenylglycinol-derived oxazolopiperidone lactams.: Enantioselective synthesis of β-substituted piperidines
    Amat, M
    Escolano, C
    Lozano, O
    Gomez-Esque, A
    Griera, R
    Molins, E
    Bosch, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (10) : 3804 - 3815
  • [4] Conjugate additions to phenylglycinol-derived unsaturated δ-lactams.: Enantioselective synthesis of uleine alkaloids
    Amat, M
    Pérez, M
    Llor, N
    Escolano, C
    Luque, FJ
    Molins, E
    Bosch, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (25) : 8681 - 8693
  • [5] Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived δ-lactam
    Amat, M
    Llor, N
    Hidalgo, J
    Escolano, C
    Bosch, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) : 1919 - 1928
  • [6] Dynamic kinetic resolution of racemic γ-aryl-δ-oxoesters.: Enantioselective synthesis of 3-arylpiperidines
    Amat, M
    Cantó, M
    Llor, N
    Escolano, C
    Molins, E
    Espinosa, E
    Bosch, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) : 5343 - 5351
  • [7] Synthesis of enantiopure trans-3,4-disubstituted piperidines.: An enantiodivergent synthesis of (+)- and (-)-paroxetine
    Amat, M
    Bosch, J
    Hidalgo, J
    Cantó, M
    Pérez, M
    Llor, N
    Molins, E
    Miravitlles, C
    Orozco, M
    Luque, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) : 3074 - 3084
  • [8] Enantioselective synthesis of 3,3-disubstituted piperidine derivatives by enolate dialkylation of phenylglycinol-derived oxazolopiperidone lactams
    Amat, Mercedes
    Lozano, Oscar
    Escolano, Carmen
    Molins, Elies
    Bosch, Joan
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (12) : 4431 - 4439
  • [9] Straightforward methodology for the enantioselective synthesis of benzo[a]- and indolo[2,3-a]quinolizidines
    Amat, Mercedes
    Santos, Maria M. M.
    Bassas, Oriol
    Llor, Nuria
    Escolano, Carmen
    Gomez-Esque, Arantxa
    Molins, Elies
    Allin, Steven M.
    McKee, Vickie
    Bosch, Joan
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) : 5193 - 5201
  • [10] Dynamic kinetic resolution and desymmetrization processes:: A straightforward methodology for the enantioselective synthesis of piperidines
    Amat, Mercedes
    Bassas, Oriol
    Llor, Nuria
    Canto, Margalida
    Perez, Maria
    Molins, Elies
    Bosch, Joan
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (30) : 7872 - 7881
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