Asymmetric Synthesis. XL.1 2,3-Disubstituted Piperidines via Chiral Non-racemic Lactams

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 849-852

  Micouin, Laurent ^a   Quirion, Jean Charles ^a   Husson, Henri Philippe ^a  

^a FACULTÉ DES SCIENCES PHARMACEUTIQUES ET BIOLOGIQUES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030053102     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02307-0     Document Type: Article

References (16)

1. For part XXXIX see : L. Micouin, M. Bonin, M.-P. Cherrier, A. Mazurier, A. Thomas, J.-C. Quirion, H.-P. Husson, Tetrahedron, submitted for publication.
2. L. Micouin, T. Varea, C. Riche, A. Chiaroni, J.-C. Quirion, H.-P. Husson, Tetrahedron Lett. 1994, 35, 2529-2532.
3. V. Schanen, A. Chiaroni, C. Riche, J.-C. Quirion, H.-P. Husson Tetrahedron Lett. 1994, 35, 2533-2536.
4. T. Varea, M. Dufour, L. Micouin, C. Riche, A. Chiaroni, J.-C. Quirion, H.-P. Husson Tetrahedron Lett. 1995, 36, 1035-1038.
5. L. Micouin, J.-C. Quirion, H.-P. Husson Angew. Chem. Int. Ed. Engl submitted to publication.
6. For a recent example of asymmetric synthesis of 2,3-disubstituted piperidines see D. Gnecco, C. Marazano, B.C. Das J. Chem. Soc. Chem. Commun. 1991, 625-627.
7. L. Micouin, J.-C. Quirion, H.-P. Husson Synth. Commun. 1996, in press
8. M. Roth, P. Dubs, E. Götschi, A. Eschenmoser Helv. Chim. Acta 1971, 54, 710-734.
9. M.J. Munchhof, A.I. Meyers J. Am. Chem. Soc. 1995, 117, 5399-5400.
10. Y.C. Hwang, M. Chu, F.W. Fowler J. Org. Chem. 1985, 50, 3885-3890.
11. 13C NMR, (δ, ppm) : 9.1 (C-3 Me), 16.1 (C-2 Me), 41.4 (C-3), 42.8 (C-6), 62.9 (C-7), 72.3 (C-8), 95.8 (C-2).
12. M; Rubiralta, E. Giralt, A. Diez "Piperidine. Structure, Preparation, Reactivity, and Synthetic Applications of Piperidine and its Derivatives", Elsevier, Amsterdam, 1991.
13. A. Stevens, Acc. Chem. Res., 1984, 17, 289-296.
14. C-2 Epimeric mixture was obtained by refluxing 5a in MeOH for 24h.
15. In these conditions, reduction was followed by hydrogenolysis of the chiral appendage. A 1/1 mixture of cis and trans 2,3-dimethyl-piperidines was obtained in 84 % yield.
16. L. Guerrier, J. Royer, D.S. Grierson, H.-P. Husson J. Am. Chem. Soc. 1983, 105, 7754-7755.