Chiral heterocyclic β-enamino esters: Convenient synthesis and diastereoselective reduction

Tetrahedron

Volumn 59, Issue 33, 2003, Pages 6333-6339

  Calvet, Sandrine ^a   David, Olivier ^a   Vanucci Bacqué, Corinne ^a   Fargeau Bellassoued, Marie Claude ^a   Lhommet, Gérard ^a  

^a CNRS   (France)

Author keywords

Debenzylation; Enamino ester; Piperidine; Pyrrolidine; Reduction; keto ester

Indexed keywords

ESTER DERIVATIVE; HETEROCYCLIC COMPOUND; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0042203687     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00980-3     Document Type: Article

References (24)

1. David O., Fargeau-Bellassoued M.-C., Lhommet G. Tetrahedron Lett. 43:2002;3471-3474.
2. (a) Ledoux S., Marchalant E., Célérier J.-P., Lhommet G. Tetrahedron Lett. 42:2001;5397-5399
3. (b) Back T.G., Hamilton M.D. Org. Lett. 4:2002;1779-1781.
4. Roth M., Dubs P., Götschi E., Eschenmoser A. Helv. Chim. Acta. 54:1971;710-734.
5. Campbell J.A., Rapoport H. J. Org. Chem. 61:1996;6313-6325.
6. Michael J.P., Hosken G.D., Howard A.S. Tetrahedron. 44:1988;3025-3036.
7. This compound was obtained according to a procedure described for the analogous ethyl ester: Lambert P.H., Vaultier M., Carrié R. J. Org. Chem. 50:1985;5352-5356.
8. 5.
9. For spectral data of 5, see: Cavé C., Daley V., d'Angelo J., Guingant A. Tetrahedron: Asymmetry. 6:1995;79-82.
10. For compound 4 see: Takahashi A., Kirio Y., Sodeoka M., Sasai H., Shibasaki M. J. Am. Chem. Soc. 111:1989;643-647.
11. 1H NMR. This result supports the initial formation of an enolate from methyl 7-chloro-3-oxoheptanoate.
12. For compound 6 see: Umemura K., Matsuyama H., Watanabe N., Kobayashi M., Kamigata N. J. Org. Chem. 54:1989;2374-2383.
13. Berthiaume G., Deslongchamps P. Bull. Soc. Chim Fr. 132:1995;371-383.
14. Andrés J.M., Herráiz-Sierra I., Pedrosa R., Pérez-Encabo A., Eur. J. Org. Chem. 2000;1719-1726.
15. (a) Bardou A., Célérier J.-P., Lhommet G. Tetrahedron Lett. 38:1997;8507-8510
16. (b) Nikiforov T., Stanchev S., Milenkov B., Dimitrov V. Heterocycles. 24:1986;1825-1829
17. (c) O'Brien P., Porter D.W., Smith N.M. Synlett. 2000;1336-1338
18. (d) Ledoux, S. PhD Thesis, Université P. et M. Curie, Paris, 2000.
19. Cimarelli C., Palmieri G. J. Org. Chem. 61:1996;5557-5563.
20. Compound 12 was purified directly by crystallization from the crude product, whereas its analogue issued from (S)-1-phenylethylamine had to be first transformed into its picrate salt to allow crystallization. See: Cusserne-Bardou, A. PhD Thesis, Université P. et M. Curie, Paris, 1997.
21. Crystallographic data (excluding structure factors) for the structure of 12 has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 202748. Copies of the data can be obtained, free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk ]. The X-ray analysis was performed in the Centre de Résolutions de Structures, Université P. et M. Curie, Paris, France.
22. Harrison J.R., O'Brien P., Porter D.W., Smith N.M. J. Chem. Soc., Perkin Trans. 1. 1999;3623-3631.
23. Kawakami T., Ohtake H., Arakawa H., Okachi T., Imada Y., Murahashi S.-I. Bull. Chem. Soc. Jpn. 73:2000;2423-2444.
24. Morley C., Knight D.W., Share A.C. J. Chem. Soc., Perkin Trans. 1. 1994;2903-2907.