Stereocontrolled addition of π-type nucleophiles to a bicyclic N-acyliminium ion. New access to trans-2,6-disubstituted piperidine substructures

Synlett

Volumn , Issue 2, 1998, Pages 206-208

  David, Marc ^a   Dhimane, Hamid ^a   Vanucci Bacqué, Corinne ^a   Lhommet, Gérard ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001589412     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1589     Document Type: Article

References (22)

1. Schneider, M. J. in Alkaloids : Chemical and Biological Perspectives ; Vol. 10 ; Ed. Pelletier, S.W. ; Pergamon Press : Oxford, 1996, pp 215-299.
2. (a) Takahata, H. ; Imose, K. ; Araya, N. ; Momose, T. Heterocycles 1994, 38, 1961.
3. (b) Jefford, C. W. ; Wang, J. B. Tetrahedron Lett. 1993, 34, 2911.
4. (c) Leclercq, S. ; Thirionet, I ; Broeders, F. ; Daloze, D. ; Van der Meer, R. ; Braeckman, J.C. Tetrahedron 1994, 50, 8465.
5. (d) Grierson, D. S. ; Royer, J. ; Guerrier, L. ; Husson, H. P. J. Org. Chemt. 1986, 51, 4475.
6. Ludwig, C. ; Wistrand, L. G. Acta Chem. Scand. 1994 , 48, 367.
7. (a) Shono, T. ; Matsumura, Y. ; Tsubata, K. ; Uchida, K. J. Org. Chem. 1986, 51, 2590.
8. (b) Irie, K. ; Aeo, K. ; Tanaka, T. ; Saito, S. J. Chem. Soc., Chem. Commun. 1985, 633.
9. (a) Thaning, M . ; Wistrand, L. G. Acta Chem. Scand. 1992, 46, 194.
10. (b) For review about stereoselective additions to N-acyliminium ions see : De Koning, H. ; Speckamp, W. N. in Methoden der Organischen Chemie (Houben-Weyl) ; Georg Thieme Verlag : Stuttgart, 1995, Vol. E21b, pp 1953-2009.
11. Dhimane, H. ; Vanucci, C. ; Lhommet, G. Tetrahedron Lett. 1997, 38, 1415.
12. 3, leading selectively to the trans azido compound has already been reported : Matsumura, Y. ; Tomita, T. Tetrahedron Lett. 1994, 35, 3737.
13. Shono, T. ; Matsumura, Y. ; Fujita, T. Tetrahedron Lett. 1991, 32, 6723.
14. 2 ; C 66.27, H 8.34, N 7.73 ; found C 66.13, H 8.37, H 7.75.
15. 2 ; C 70.29, H 6.29, N 10.93 ; found C 70.20, H 6.32, N 10.99.
16. 13C NMR, optical rotation and elemental analysis.
17. 13C NMR were recorded on a Bruker ARX 250 apparatus equipped with a reverse probe. Analytical GC were performed on a Delsi 30 apparatus equipped with a split-mode capillary injection system and a flame ionisation detector. Fused silica column CPSIL 5 (Chrompack) (25 m x 250 μm) was used.
18. The authors have deposited atomic coordinates for Sb with the Cambridge Crystallographic Data Center. They can be obtained, on request, from the Director, Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ, UK.
19. Gaudemer, A. in Stereochemistry : Fundamentals and Methods ; Vol. 1 ; Ed. Kagan, H.B., Georg Thieme : Stuttgart, 1977, p 94.
20. 13C-α signal appears at 50 ppm is believed to have a trans stereochemistry .
21. 2 character of the nitrogen atom, conformation B shown in figure 2 is precluded.
22. Deslongchamps, P. in Stereoelectronic Effects in Organic Chemistry, Pergamon : New York, 1983, Chapter 6.