Diastereoselective synthesis of 2,6-trans-disubstituted piperidines via sequential cross-metathesis-cationic cyclisation

Advanced Synthesis and Catalysis

Volumn 349, Issue 1-2, 2007, Pages 157-160

  Mix, Stefan ^a   Blechert, Siegfried ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

2,6 disubstituted piperidines; 3,5 disubstituted indolizidines; 6 endo trig cyclisation; Cationic cyclisation; Cross metathesis; Ruthenium

Indexed keywords

EID: 33846686836     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200600482     Document Type: Article

References (35)

1. a) E. A. Gerson, R. G. Kelsey, Biochemical Systematics and Ecology, 2004, 32, 63;
2. b) D. O'Hagan, Nat. Prod. Rep. 2000, 17, 435;
3. c) D. O'Hagan, Nat. Prod. Rep. 1997, 14, 637;
4. d) M. Pan, T. J. Mabry, J. M. Beale, B. M. Mamiya, Phytochemistry 1997, 45, 517;
5. e) S. Leclerq, J. C. Braekman, D. Daloze, J. M. Pasteels, R. K. Van der Meer, Naturwissenschaften 1996, 83, 222.
6. Selected reviews: a) J. P. A. Harrity, O. Provoost, Org. Biomol. Chem. 2005, 3, 1349;
7. b) M. G. P. Buffat, Tetrahedron 2004, 60, 1701;
8. c) F.-X. Felpin, J. Lebreton, Current Organic Synthesis 2004, 1, 83-109;
9. S. Laschat, T. Dickner, Synthesis 2000, 13, 1781-1813;
10. e) A. Mitchison, A. Nadin, J. Chem. Soc., Perkin Trans. 1 1999, 2553;
11. f) A. Nadin, J. Chem. Soc., Perkin Trans. 1 1998, 3493;
12. g) M. Bols, Acc. Chem. Res. 1998, 31, 1;
13. h) U. Kazmaier, Recent Res. Dev. Org. Chem. 1998, 2, 351;
14. S. Leclercq, D. Daloze, J.-C. Braekman, Org. Prep. Proced. Int. 1996, 28, 501.
15. a) P. Dewi-Wülfling, J. Gebauer, S. Blechert, Synlett 2006, 3, 487;
16. b) J. Gebauer, S. Blechert, Synlett 2005, 18, 2826;
17. J. Gebauer, P. Dewi, S. Blechert, Tetrahedron Lett. 2005, 46, 43;
18. S. Randl, S. Blechert, Tetrahedron Lett. 2004, 45, 1167.
19. a) S. Randl, S. Blechert, J. Org. Chem. 2003, 68, 8879.
20. a) Y. Hirai, J. Watanabe, T. Nozaki, H. Yokoyama, S. Yamaguchi, J. Org. Chem. 1997, 62, 776;
21. b) Y. Hirai, K. Shibuya, Y. Fukuda, H. Yokoyama, S. Yamaguchi, Chem. Lett. 1997, 221;
22. K. Takao, Y. Nigawara, E. Nishino, I. Takagi, K. Maeda, K. Tadano, S. Ogawa, Tetrahedron 1994, 50, 5681.
23. Prepared according to: Q. B. Broxterman, B. Kaptein, J. Kamphuis, H. E. Schoemaker, J. Org. Chem. 1992, 57, 6286.
24. Prepared according to: J. Pernerstorfer, M. Schuster, S. Blechert, Chem. Commun. 1997, 1949.
25. Prepared according to: N. J. Turner, G. M. Whitesides, J. Am. Chem. Soc. 1989, 111, 624.
26. Prepared according to: C. J. Easton, S. C. Peters, Tetrahedron Lett. 1992, 33, 5581.
27. Prepared according to: S. C. G. Biagini, S. E. Gibson, S. P. Keen, J. Chem. Soc., Perkin Trans. 1 1998, 16, 2485.
28. NMR data for the N-benzyl analogue are given by: P. D. Bailey, G. R. Brown, F. Korber, A. Reed, R. D. Wilson, Tetrahedron: Asymmetry 1991, 2, 1263.
29. a) T. J. Wilkinson, N. W. Stehle, P. Beak, Org. Lett. 2000, 2, 155;
30. b) M. T. Reding, S. L. Buchwald, J. Org. Chem. 1998, 63, 6344.
31. a) J. S. T. Gorman, T. H. Jones, T. F. Spande, R. R. Snelling, J. A. Torres J. Chem. Ecol. 1998, 24, 933;
32. b) T. H. Jones, R. J. Highet, M. S. Blum, H. M. Fales, J. Chem. Ecol. 1984, 10, 1233.
33. a) H. Takahata, H. Bandoh, T. Momose, Tetrahedron 1993, 49, 11205;
34. [4,][13a]
35. K. Shishido, M. Shindo, Y. Fukuda, Org. Lett. 2003, 5, 749.