Stereoselective 5-exo-trig radical cyclization in the enantioselective synthesis of Pregabalin

Tetrahedron Letters

Volumn 48, Issue 24, 2007, Pages 4305-4308

  Rodríguez, Verónica ^a   Quintero, Leticia ^a   Sartillo Piscil, Fernando ^a  

^a BENEMÉRITA UNIVERSIDAD AUTÓNOMA DE PUEBLA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

PREGABALIN;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; RADICAL REACTION; STEREOCHEMISTRY;

EID: 34249095432     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.04.054     Document Type: Article

References (28)

1. Yuen P., Kanter G.D., Taylor C.-P., and Vartanian M.G. Bioorg. Med. Chem. Lett. 4 (1994) 823-826
2. Bryans J.S., Davies N., Gee N.S., Dissanayake V.U.K., Ratcliffe G.S., Horwell D.C., Kneen C.O., Morrel A.I., Oles R.J., O'Toole J.C., Perkins G.M., Singh L., Suman-Chauhan N., and O'Neill J.A. J. Med. Chem. 41 (1998) 1838-1845
3. Butters M., Catterick D., Craig A., Curzons A., Dale D., Gillmore A., Green S.P., Marziano I., Sherlock J.-P., and White W. Chem. Rev. 106 (2006) 3002-3027
4. Taylor C.P. In: Chadwick D. (Ed). New Trends in Epilepsy Management (1993), Royal Society of Medicine Services Ltd, London 13-40
5. Hoekstra M.S., Sobieray D.M., Schwindt M.A., Mulhern T.A., Grote T.M., Huckabee B.K., Hendrickson V.S., Franklin L.C., Granger E.J., and Karrick G.L. Org. Process Res. Dev. 1 (1997) 26-38
6. Burk M.J., de Koning P.D., Grote T.M., Hoekstra M.S., Hoge G., Jennings R.A., Kissel W.S., Le T.V., Lennon I.C., Mulhern T.A., Ramsden J.A., and Wade R.A. J. Org. Chem. 68 (2003) 5731-5734
7. Hoge G., Wu H.-P., Kissel W.S., Pflum D.A., Greene D.J., and Bao J. J. Am. Chem. Soc. 126 (2004) 5966-5967
8. Rodriguez V., Sánchez M., Quintero L., and Sartillo-Piscil F. Tetrahedron 60 (2004) 10809-10815
9. See previous work of Orena:. Cardillo B., Galeazzi R., Mobbili G., Orena M., and Rossetti M. Heterocycles 38 (1994) 2663-2676
10. Similar results were observed by. Ishibashi H., Fuke Y., Yamashita T., and Ikeda M. Tetrahedron: Asymmetry 7 (1996) 2531-2538
11. Juaristi E., León-Romo J.L., Reyes A., and Escalante J. Tetrahedron: Asymmetry 10 (1999) 2441-2495
12. Curran D.P., Porter N.A., and Giese B. Stereochemistry of Radical Reactions (1995), VCH, Eeinheim
13. Sibi M.P., and Porter N.A. Acc. Chem. Res. 32 (1999) 163-171
14. Porter N.A., Giese B., and Curran D.P. Acc. Chem. Res. 24 (1991) 296-304
15. Renaud P., and Gerster M. Angew. Chem., Int. Ed. 37 (1998) 2562-2579 and references cited therein
16. Murakata M., Jono T., Mizuno Y., and Hoshino O. J. Am. Chem. Soc. 119 (1997) 11713-11714
17. Nishida M., Hayashi H., Yamaura Y., Yanaginuma E., and Yonemitsu O. Tetrahedron Lett. 36 (1995) 269-272
18. Nishida M., Ueyama E., Hayashi H., Ohtake Y., Yamaura Y., Yanaginuma E., Yonemutsu O., Nishida A., and Kawahara N. J. Am. Chem. Soc. 116 (1994) 6455-6456
19. Badone D., Bernassau J.-M., Cardamone R., and Guzzi U. Angew. Chem., Int. Ed. 35 (1996) 535-538
20. Enholm E.J., and Cottone J.S. Org. Lett. 3 (2001) 3959-3962
21. Nishida M., Hayashi H., Yamaura Y., Yanaginuma E., and Yonemitsu O. Tetrahedron Lett. 36 (1995) 269-272
22. Nishida M., Ueyama E., Hayashi H., Ohtake Y., Yamaura Y., Yanaginuma E., Yonemutsu O., Nishida A., and Kawahara N. J. Am. Chem. Soc. 116 (1994) 6455-6456
23. Badone D., Bernassau J.-M., Cardamone R., and Guzzi U. Angew. Chem., Int. Ed. 35 (1996) 535-538
24. Enholm E.J., Cottone J.S., and Allais F. Org. Lett. 3 (2001) 145-147
25. Keum G., Kang S.B., Kim Y., and Lee E. Org. Lett. 6 (2004) 1895-1897
26. Meyers A.I., and Snyder L. J. Org. Chem. 58 (1993) 36-42
27. Kamimura A., Omata Y., Tanaka K., and Shirai M. Tetrahedron 59 (2003) 6291-6299
28. The existence of a weak internal hydrogen bond between Hα and the carbonyl group has been determined by computational calculations for chiral amide 5. See Ref. 5. Additionally see the work of Hanessian, which has been invoked hydrogen bonding as a stereocontrol element in radical reactions:. Hanessian S., Yang H., and Schaum R. J. Am. Chem. Soc. 118 (1996) 2507-2508