Free radical-mediated vinyl amination: A mild, general pyrrolidinyl enamine synthesis

Tetrahedron

Volumn 59, Issue 45, 2003, Pages 8877-8888

  Nugent, Benjamin M ^a   Williams, Amie L ^a   Prabhakaran, E N ^a   Johnston, Jeffrey N ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

Alkyne aminostannation; Enamines; Free radicals; Vinyl amination; stannyl enamine

Indexed keywords

AZO COMPOUND; ENAMINE; FREE RADICAL; NITROGEN; PYRROLIDINYL ENAMINE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

AMINATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; INFRARED RADIATION; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0142186309     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.04.003     Document Type: Article

References (46)

1. (a) Stork G., Brizzolara A., Landesman H., Szmuszkovicz J., Terrell R. J. Am. Chem. Soc. 85:1963;207
2. (b) Stork G., Terrell R.J., Szmuszkovicz J. J. Am. Chem. Soc. 76:1954;2029
3. (c) Stork G. Med. Res. Rev. 19:1999;370.
4. (a) Mayr H., Bug T., Gotta M.F., Hering N., Irrgang B., Janker B., Kempf B., Loos R., Ofial A.R., Remennikov G., Schimmel H. J. Am. Chem. Soc. 123:2001;9500
5. (b) Mayr H., Patz M. Angew. Chem. Int. Ed. Engl. 33:1994;938.
6. March J. Advanced Organic Chemistry. 4th ed. 1992;Wiley, New York. pp 897-898 and references therein.
7. Li T., Marks J. J. Am. Chem. Soc. 120:1998;1757.
8. Petasis N.A., Lu S.-P. Tetrahedron Lett. 36:1995;2393.
9. (a) Cloke J.B. J. Am. Chem. Soc. 51:1929;1174
10. (b) Stevens R.V., Ellis M.C., Wentland M.P. J. Am. Chem. Soc. 90:1968;5576-5580
11. (c) Prevost N., Shipman M. Org. Lett. 3:2001;2383.
12. Vinyl bromide coupling with resonance stabilized amines: (a) Lam P.Y.S., Duedon S., Averill K.M., Li R., He M.Y., DeShong P., Clark C.G. J. Am. Chem. Soc. 122:2000;7600 (b) Lam P.Y.S., Vincent G., Clark C.G., Deudon S., Jadhav P.K. Tetrahedron Lett. 42:2001;3415 (c) Lebedev A.Y., Izmer V.V., Kazyul'kin D.N., Beletskaya I.P., Voskoboynikov A.Z. Org. Lett. 4:2002;623.
13. Vinyl bromide coupling with resonance stabilized amines: (a) Lam P.Y.S., Duedon S., Averill K.M., Li R., He M.Y., DeShong P., Clark C.G. J. Am. Chem. Soc. 122:2000;7600 (b) Lam P.Y.S., Vincent G., Clark C.G., Deudon S., Jadhav P.K. Tetrahedron Lett. 42:2001;3415 (c) Lebedev A.Y., Izmer V.V., Kazyul'kin D.N., Beletskaya I.P., Voskoboynikov A.Z. Org. Lett. 4:2002;623.
14. Vinyl bromide coupling with resonance stabilized amines: (a) Lam P.Y.S., Duedon S., Averill K.M., Li R., He M.Y., DeShong P., Clark C.G. J. Am. Chem. Soc. 122:2000;7600 (b) Lam P.Y.S., Vincent G., Clark C.G., Deudon S., Jadhav P.K. Tetrahedron Lett. 42:2001;3415 (c) Lebedev A.Y., Izmer V.V., Kazyul'kin D.N., Beletskaya I.P., Voskoboynikov A.Z. Org. Lett. 4:2002;623.
15. Barluenga J., Fernández M.A., Aznar F., Valdés C. Chem. Commun. 2002;2362.
16. (a) Wolfe J.P., Wagaw S., Marcoux J.-F., Buchwald S.L. Acc. Chem. Res. 31:1998;805
17. (b) Hartwig J.F. Pure Appl. Chem. 71:1999;1417
18. (c) Yang B.H., Buchwald S.L. J. Organomet. Chem. 576:1999;125.
19. (a) Takano S., Suzuki M., Kijima A., Ogasawara K. Chem. Lett. 1990;315
20. (b) Takano S., Suzuki M., Ogasawara K. Heterocycles. 37:1994;149.
21. (a) Tomaszewski M.J., Warkentin J. Tetrahedron Lett. 1992;2123
22. (b) Tomaszewski M.J., Warkentin J., Werstiuk N.H. Aust. J. Chem. 48:1995;291.
23. For additional examples of carbon radical additions to azomethine nitrogen, see: (a). (e) Review of carbon radical additions to azomethine derivatives: For additional examples of carbon radical additions to azomethine nitrogen, see: (a) Bowman W.R., Stephenson P.T., Terrett N.K., Young A.R. Tetrahedron Lett. 35:1994;6369 (b) Bowman W.R., Stephenson P.T., Terrett N.K., Young A.R. Tetrahedron. 51:1995;7959 (c) McClure C.K., Kiessling A.J., Link J.S. Tetrahedron. 54:1998;7121 (d) Orito K., Uchiito S., Satoh Y., Tatsuzawa T., Harada R., Tokuda M. Org. Lett. 2:2000;307. (e) Review of carbon radical additions to azomethine derivatives: Friestad G.K. Tetrahedron. 57:2001;5461.
24. For additional examples of carbon radical additions to azomethine nitrogen, see: (a). (e) Review of carbon radical additions to azomethine derivatives: For additional examples of carbon radical additions to azomethine nitrogen, see: (a) Bowman W.R., Stephenson P.T., Terrett N.K., Young A.R. Tetrahedron Lett. 35:1994;6369 (b) Bowman W.R., Stephenson P.T., Terrett N.K., Young A.R. Tetrahedron. 51:1995;7959 (c) McClure C.K., Kiessling A.J., Link J.S. Tetrahedron. 54:1998;7121 (d) Orito K., Uchiito S., Satoh Y., Tatsuzawa T., Harada R., Tokuda M. Org. Lett. 2:2000;307. (e) Review of carbon radical additions to azomethine derivatives: Friestad G.K. Tetrahedron. 57:2001;5461.
25. For additional examples of carbon radical additions to azomethine nitrogen, see: (a). (e) Review of carbon radical additions to azomethine derivatives: For additional examples of carbon radical additions to azomethine nitrogen, see: (a) Bowman W.R., Stephenson P.T., Terrett N.K., Young A.R. Tetrahedron Lett. 35:1994;6369 (b) Bowman W.R., Stephenson P.T., Terrett N.K., Young A.R. Tetrahedron. 51:1995;7959 (c) McClure C.K., Kiessling A.J., Link J.S. Tetrahedron. 54:1998;7121 (d) Orito K., Uchiito S., Satoh Y., Tatsuzawa T., Harada R., Tokuda M. Org. Lett. 2:2000;307. (e) Review of carbon radical additions to azomethine derivatives: Friestad G.K. Tetrahedron. 57:2001;5461.
26. For additional examples of carbon radical additions to azomethine nitrogen, see: (a). (e) Review of carbon radical additions to azomethine derivatives: For additional examples of carbon radical additions to azomethine nitrogen, see: (a) Bowman W.R., Stephenson P.T., Terrett N.K., Young A.R. Tetrahedron Lett. 35:1994;6369 (b) Bowman W.R., Stephenson P.T., Terrett N.K., Young A.R. Tetrahedron. 51:1995;7959 (c) McClure C.K., Kiessling A.J., Link J.S. Tetrahedron. 54:1998;7121 (d) Orito K., Uchiito S., Satoh Y., Tatsuzawa T., Harada R., Tokuda M. Org. Lett. 2:2000;307. (e) Review of carbon radical additions to azomethine derivatives: Friestad G.K. Tetrahedron. 57:2001;5461.
27. For additional examples of carbon radical additions to azomethine nitrogen, see: (a). (e) Review of carbon radical additions to azomethine derivatives: For additional examples of carbon radical additions to azomethine nitrogen, see: (a) Bowman W.R., Stephenson P.T., Terrett N.K., Young A.R. Tetrahedron Lett. 35:1994;6369 (b) Bowman W.R., Stephenson P.T., Terrett N.K., Young A.R. Tetrahedron. 51:1995;7959 (c) McClure C.K., Kiessling A.J., Link J.S. Tetrahedron. 54:1998;7121 (d) Orito K., Uchiito S., Satoh Y., Tatsuzawa T., Harada R., Tokuda M. Org. Lett. 2:2000;307. (e) Review of carbon radical additions to azomethine derivatives: Friestad G.K. Tetrahedron. 57:2001;5461.
28. Johnston J.N., Plotkin M.A., Viswanathan R., Prabhakaran E.N. Org. Lett. 3:2001;1009.
29. Viswanathan R., Prabhakaran E.N., Plotkin M.A., Johnston J.N. J. Am. Chem. Soc. 125:2003;163.
30. Prabhakaran E.N., Cox A.L., Nugent B.M., Nailor K.E., Johnston J.N. Org. Lett. 4:2002;4197.
31. Cox A.L., Johnston J.N. Org. Lett. 3:2001;3695.
32. Smithers R.H. J. Org. Chem. 43:1978;2833.
33. O'Donnell M.J. Catalytic Asymmetric Synthesis. 2nd ed. 2000;Wiley, New York. Chapter 10 O'Donnell M.J., Polt R.L. J. Org. Chem. 47:1982;2663.
34. O'Donnell M.J. Catalytic Asymmetric Synthesis. 2nd ed. 2000;Wiley, New York. Chapter 10 O'Donnell M.J., Polt R.L. J. Org. Chem. 47:1982;2663.
35. Trost B.M., Chen D.W.C. J. Am. Chem. Soc. 118:1996;12541.
36. Sampson P.B., Honek J.F. Org. Lett. 1:1999;1395.
37. Lukes R., Dedek V., Novotny L. Collect. Czech. Chem. Commun. 24:1959;1117.
38. Preparation and reactivity of isoindoles (review): Donohoe T.J. Sci. Synth. 10:2001;653.
39. (a) Alberti A., Bedofni N., Benaglia M., Leardini R., Nanni D., Pedulli G.F., Tundo A., Zanardi G. J. Org. Chem. 57:1992;607
40. (b) Leardini R., Lucarini M., Nanni D., Pedulli G.F., Tundo A., Zanardi G. J. Org. Chem. 58:1993;2419
41. (c) Benati L., Placucci G., Spagnolo P., Tundo A., Zanardi G. J. Chem. Soc. Perkin Trans. 1. 1977;1684.
42. Kim S., Joe S.H., Do J.Y. J. Am. Chem. Soc. 116:1994;5521.
43. Ryu I., Ogura S., Minakata S., Komatsu M. Tetrahedron Lett. 40:1999;1515.
44. Shi L., Narula C.K., Mak K.T., Kao L., Xu Y., Heck R.F. J. Org. Chem. 48:1983;3894.
45. Pickard P.L., Tolbert T.L. Organic Syntheses. Collect. Vol. 5:1973;Wiley, New York. pp 520-522.
46. Procedures and spectroscopic details for all compounds can be found in Ref. 15.