Access to 2,6-disubstituted piperidines: Control of the diastereoselectivity, scope, and limitations. applications to the stereoselective synthesis of (-)-solenopsine A and alkaloid (+)-241D

Journal of Organic Chemistry

Volumn 78, Issue 6, 2013, Pages 2511-2526

  Abrunhosa Thomas, Isabelle ^a,b   Plas, Aurélie ^a,b   Vogrig, Alexandre ^a,b   Kandepedu, Nishanth ^a,b   Chalard, Pierre ^a,b   Troin, Yves ^a,b  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

^b ICCF   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE; INTRAMOLECULAR REACTIONS; STEREOSELECTIVE SYNTHESIS; TOTAL SYNTHESIS; UNSATURATED KETONES;

ALKALOIDS; KETONES; METABOLITES; NITROGEN COMPOUNDS; STEREOCHEMISTRY;

STEREOSELECTIVITY;

ALKALOID; BENZYL 4 (DIETHOXYPHOSPHORYL) 3 OXO 1 PHENYLBUTYLCARBA; BENZYL 5 (DIETHOXYPHOSPHORYL) 4 OXOPENTAN 2 YLCARBAMATE; BETA CARBAMATE ALPHA BETA UNSATURATED KETONE; ETHYL 1 (DIETHOXYPHOSPHORYL) 2 OXODODECAN 4 YLCARBAMATE; ETHYL 1 (DIETHOXYPHOSPHORYL) 2 OXOHEPTAN 4 YLCARBAMATE; ETHYL 4 (DIETHOXYPHOSPHORYL) 3 OXO 1 PHENYLBUTYLCARBAMATE; ETHYL 4 OXO 6 (PYRIDIN 3 YL)HEX 5 EN 2 YLCARBAMATE; ETHYL 4 OXO 6 PHENYL HEX 5 EN 2 YLCARBAMATE; ETHYL 4 OXO NON 5 EN 2 YLCARBAMATE; ETHYL 4 OXO TETRADEC 5 EN 2 YLCARBAMATE; ETHYL 5 (DIETHOXYPHOSPHORYL) 4 OXOPENTAN 2 YLCARBAMATE; ETHYL 6 (2 NITROPHENYL) 4 OXOHEX 5 EN 2 YLCARBAMATE; ETHYL 6 (3 NITROPHENYL) 4 OXOHEX 5 EN 2 YLCARBAMATE; ETHYL 6 (4 BROMOPHENYL) 4 OXO HEX 5 EN 2 YLCARBAMATE; ETHYL 6 (4 METHOXYPHENYL) 4 OXOHEX 5 EN 2 YLCARBAMATE; ETHYL 6 (4 NITROPHENYL) 4 OXOHEX 5 EN 2 YLCARBAMATE; ETHYL 6 (ETHOXYCARBONYLAMINO) 4 OXOHEPT 2 ENOATE; ETHYL 8 (ETHOXYCARBONYLAMINO) 6 OXO NONA 2,4 DIENOATE; KETONE DERIVATIVE; METHYL 3 (BENZYLOXYCARBONYLAMINO) 3 PHENYLPROPANOATE; METHYL 3 (BENZYLOXYCARBONYLAMINO)BUTANOATE; METHYL 3 (ETHOXYCARBONYLAMINO) 3 PHENYLPROPANOATE; METHYL 3 (ETHOXYCARBONYLAMINO)BUTANOATE; METHYL 3 (ETHOXYCARBONYLAMINO)UNDECANOATE; METHYL 3 (TERT BUTOXYCARBONYLAMINO) 3 PHENYLPROPANOATE; PIPERIDINE DERIVATIVE; SOLENOPSINE A; TERT BUTYL 4 (DIETHOXYPHOSPHORYL) 3 OXO 1 PHENYLBUTYLCARBAMATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATION; COVALENT BOND; CYCLIZATION; DRUG SYNTHESIS; HYDROGENATION; ISOMER; STEREOCHEMISTRY; STOICHIOMETRY; WITTIG HORNER EMMON REACTION;

ALKALOIDS; CATALYSIS; KETONES; MOLECULAR STRUCTURE; PIPERIDINES; STEREOISOMERISM;

EID: 84875153543     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302712f     Document Type: Article

References (49)

1. Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: Oxford, U.K., 1996; Vol. 10.
2. Laschat, S.; Dickner, T. Synthesis 2000, 13, 1781-1813
3. Ghorai, M. K.; Halder, S.; Das, R. K. J. Org. Chem. 2010, 75, 7061-7072
4. Guérinot, A.; Serra-Muns, A.; Gnamm, C.; Bensoussan, C.; Reymond, S.; Cossy, J. Org. Lett. 2010, 12, 1808-1811
5. Ragoussi, M.-E.; Walker, S. M.; Picanello, A.; Kariuki, B. M.; Horton, P. N.; Spencer, N.; Snaith, J. S. J. Org. Chem. 2010, 75, 7347-7357
6. Agami, C.; Couty, F.; Evano, G.; Darro, F.; Kiss, R. Eur. J. Org. Chem. 2003, 2062-2070
7. Felpin, F.-X.; Lebreton, J. Tetrahedron 2004, 60, 10127-10153
8. Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J.-C. Tetrahedron: Asymmetry 1998, 9, 4361-4368
9. Rougnon-Glasson, S.; Tratrat, C.; Canet, J.-L.; Chalard, P.; Troin, Y. Tetrahedron: Asymmetry 2004, 15, 1561-1567
10. Dolman, S. J.; Sattely, E. S.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 2002, 124, 6991-6994
11. Jorgensen, K. A. Angew. Chem., Int. Ed. 2000, 39, 3558-3588
12. Singh, O. V.; Han, H. Org. Lett. 2004, 6, 3067-3070
13. Daly, M.; Cant, A. A.; Fowler, L. S.; Simpson, G. L.; Senn, H. M.; Sutherland, A. J. Org. Chem. 2012, 77, 10001-10009
14. Davis, F. A.; Rao, A.; Carroll, P. J. Org. Lett. 2003, 5, 3855-3857
15. Leijondahl, K.; Borén, L.; Braun, R.; Bäckvall, J.-E. J. Org. Chem. 2009, 74, 1988-1993
16. Jung, H. H.; Floreancig, P. E. J. Org. Chem. 2007, 72, 7359-7366
17. Gnamm, C.; Krauter, C. M.; Brödner, K.; Helmchen, G. Chem.-Eur. J. 2009, 15, 2050-2054
18. Agami, C.; Comesse, S.; Kadouri-Puchot, C. J. Org. Chem. 2002, 67, 2424-2428
19. Ishimaru, K.; Yamamoto, Y.; Akiba, K. Tetrahedron 1997, 53, 5423-5432
20. Ahman, J.; Jarevang, T.; Somfai, P. J. Org. Chem. 1996, 61, 8148-8159
21. Raghavan, S.; Mustafa, S. Tetrahedron Lett. 2008, 49, 5169-5171
22. Wynne, E. L.; Clarkson, G. J.; Shipman, M. Tetrahedron Lett. 2008, 49, 250-252
23. Grierson, D. S.; Royer, J.; Guerrier, L.; Husson, H. P. J. Org. Chem. 1986, 51, 4475-4477
24. Comins, D. L.; Hong, H. J. Am. Chem. Soc. 1993, 115, 8851-8852
25. Oppolzer, W.; Bocher, C. G.; Merifield, E. Tetrahedron Lett. 1994, 35, 7015-7018
26. Takahata, H.; Yotsui, Y.; Momose, T. Tetrahedron 1998, 54, 13505-13516
27. David, M.; Dhimane, H.; Vanucci-Bacque, C.; Lhommet, G. J. Org. Chem. 1999, 64, 8402-8405
28. Amat, M.; Llor, N.; Hidalgo, J.; Escolano, C.; Bosch, J. J. Org. Chem. 2003, 68, 1919-1928
29. Girard, N.; Hurvois, J. P. Synth. Commun. 2005, 35, 711-723
30. Davis, F. A.; Xu, H.; Zhang, J. J. Org. Chem. 2007, 72, 2046-2052
31. Abrunhosa-Thomas, I.; Roy, O.; Barra, M.; Besset, T.; Chalard, P.; Troin, Y. Synlett 2007, 1613-1615
32. Wadsworth, W. S.; Emmons, W. D. Organic Synthesis; Wiley: New York, 1973; Collect. Vol. V, pp 547-563.
33. Bariau, A.; Canet, J.-L.; Chalard, P.; Troin, Y. Tetrahedron: Asymmetry 2005, 16, 3650-3660
34. Davis, F. A.; Zhang, J.; Qiu, H.; Wu, Y. Org. Lett. 2008, 10, 1433-1436
35. Boeglin, D.; Heitz, A.; Martinez, J.; Fehrentz, J.-A. Eur. J. Org. Chem. 2003, 3139-3146
36. Paterson, I.; Lyothier, I. Org. Lett. 2004, 6, 4933-4936
37. Modica, E.; Compostella, F.; Colombo, D.; Franchini, L.; Cavallari, M.; Mori, L.; De Libero, G.; Panza, L.; Ronchetti, F. Org. Lett. 2006, 8, 3255-3258
38. Banwell, M. G.; Bisset, B. D.; Bui, C. T.; Pham, H. T. T.; Simpson, G. W. Aust. J. Chem. 1998, 51, 9-18
39. Moriyama, Y.; Doan-Huynh, D.; Monneret, C.; Khuong-Huu, Q. Tetrahedron Lett. 1977, 10, 825-828
40. Takahata, H.; Saito, Y.; Ichinose, M. Org. Biomol. Chem. 2006, 4, 1587-1595
41. Cheînevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341
42. Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503-2505
43. Montfray, J.; Gelas-Mialhe, Y.; Gramain, J.-C.; Remuson, R. Tetrahedron: Asymmetry 2005, 16, 1025-1034
44. Ciblat, S.; Besse, P.; Papastergiou, V.; Veschambre, H.; Canet, J.-L.; Troin, Y. Tetrahedron: Asymmetry 2000, 11, 2221-2229
45. Cooper, J.; Knight, D. W.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1991, 705-713
46. Fleck, T. J.; McWhorter, W. W.; DeKam, R. N.; Pearlman, B. A. J. Org. Chem. 2003, 68, 9612-9617
47. Lou, S.; Dai, P.; Schaus, S. E. J. Org. Chem. 2007, 72, 9998-10008
48. Takahata, H.; Ouchi, H.; Ichinose, M.; Nemoto, H. Org. Lett. 2002, 4, 3459-3462
49. Jefford, C. W.; Jian, B. W. Tetrahedron Lett. 1993, 34, 2911-2914