Stereoselective α-amidoalkylation of phenylglycinol-derived lactams. Synthesis of enantiopure 5,6-disubstituted 2-piperidones

Tetrahedron Asymmetry

Volumn 17, Issue 10, 2006, Pages 1581-1588

  Amat, Mercedes ^a   Escolano, Carmen ^a   Gómez Esqué, Arantxa ^a   Lozano, Oscar ^a   Llor, Núria ^a   Griera, Rosa ^a   Molins, Elies ^b   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b INSTITUT DE CIÈNCIA DE MATERIALS DE BARCELONA ICMAB CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLTRIMETHYLSILANE; INDOLE; LACTAM DERIVATIVE; PIPERIDONE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; GRIGNARD REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 33745423767     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.05.018     Document Type: Article

References (20)

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12. For a related study in the oxazolopyrrolidone series, see:. Baussanne I., Chiraroni A., and Royer J. Tetrahedron: Asymmetry 12 (2001) 1219-1224
13. Amat M., Llor N., Hidalgo J., and Bosch J. Tetrahedron: Asymmetry 8 (1997) 2237-2240
14. For a similar equilibration in the de-ethyl series, see:. Amat M., Bosch J., Hidalgo J., Cantó M., Pérez M., Llor N., Molins E., Miravitlles C., Orozco M., and Luque J. J. Org. Chem. 65 (2000) 3074-3084
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16. For recent reviews on the chemistry of N-acyliminium ions, see:. Speckamp W.N., and Moolenaar M.J. Tetrahedron 56 (2000) 3817-3856
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18. The triallyl derivative 4c, formed by attack of the Grignard reagent to the initially formed lactam 4a, was also isolated.
19. Amat M., Hadida S., Llor N., Sathyanarayana S., and Bosch J. J. Org. Chem. 61 (1996) 3878-3882
20. Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 607207. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (0)1223 336033 or e-mail: deposit@ccdc.cam.ac.uk].