Synthesis of 2,3-disubstituted pyrrolidines by intramolecular addition of α-aminoalkyl radicals to electron deficient C=C bonds

Tetrahedron

Volumn 55, Issue 23, 1999, Pages 7345-7362

  Aurrecoechea, José M ^a   Fernández, Alvaro ^a   Gorgojo, José M ^a   Saornil, Carlos ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Cyclization; Pyrrolidines; Radicals; Samarium

Indexed keywords

ALKYL GROUP; N BENZYL 2 DECYL 3 (ETHOXYCARBONYLMETHYL)PYRROLIDINE; PYRROLIDINE DERIVATIVE; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; DIMERIZATION; ELECTRON TRANSPORT; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0033523072     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00359-2     Document Type: Article

References (96)

1. Some recent references: (a) Ganem, B. Acc. Chem. Res. 1996, 29, 340-347.
2. (b) Bachi, M. D.; Melman, A. J. Org. Chem. 1997, 62, 1896-1898.
3. (c) O'Hagan, D. Nat. Prod. Rep. 1997, 14, 637-651.
4. (d) Miyata, O.; Ozawa, Y.; Ninomiya, I.; Naito, T. Synlett 1997, 275-276.
5. (e) Sato, Y.; Saito, N.; Mori, M. Tetrahedron Lett. 1997, 38, 3931-3934.
6. (f) Lee, R. E.; Smith, M. D.; Nash, R. J.; Griffiths, R. C.; Mcneil, M.; Grewal, R. K.; Yan, W. X.; Besra, G. S.; Brennan, P. J.; Fleet, G. W. J. Tetrahedron Lett. 1997, 38, 6733-6736.
7. (g) Bols, M. Acc. Chem. Res. 1998, 31, 1-8.
8. (h) Carretero, J. C.; Arrayas, R. G. J. Org. Chem. 1998, 63, 2993-3005.
9. (i) Pearson, W. H.; Lovering, F. E. J. Org. Chem. 1998, 63, 3607-3617.
10. (j) Mukai, C.; Sugimoto, Y.; Miyazawa, K.; Yamaguchi, S.; Hanaoka, M. J. Org. Chem. 1998, 63, 6281-6287.
11. A recent review: Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825-1872.
12. General reviews: (a) Curran, D. P. Synthesis 1988, 417-439.
13. (b) Curran, D. P. Synthesis 1988, 489-513.
14. (c) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237-1286.
15. (d) Koert, U. Angew. Chem. Int. Ed. Engl. 1996, 35, 405-407.
16. (e) Giese, B.; Kopping, B.; Göbel, T.; Dickhant, J.; Thoma, G.; Kulicke, K. J.; Trach, F. in Organic Reactions; Paquette, L. A. Ed.; John Wiley & Sons: New York, 1996; Vol. 48; pp 301-856.
17. (f) Aldabbagh, F.; Bowman, W. R. Contemp. Org. Synth. 1997, 4, 261-280.
18. A recent review: Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543-17594.
19. A review: (a) Renaud, P.; Giraud, L. Synthesis 1996, 913-926.
20. Recent references: (b) Clive, D. L. J.; Yang, W. Chem. Commun. 1996, 1605-1606.
21. (c) Della, E. W.; Knill, A. M.; Smith, P. A. Chem. Commun. 1996, 1637-1638.
22. (d) Pandey, G.; Reddy, G. D.; Chakrabarti, D. J Chem. Soc., Perkin Trans. 1 1996, 219-224.
23. (e) Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc., Perkin Trans. 1 1996, 465-473.
24. (f) Ikeda, M.; Kugo, Y.; Sato, T. J. Chem. Soc., Perkin Trans. 1 1996, 1819-1824.
25. (g) Rios, L. A.; Dolbier, W. R.; Paredes, R.; Lusztyk, J.; Ingold, K. U.; Jonsson, M. J. Am. Chem. Soc. 1996, 118, 11313-11314.
26. (h) Robertson, J.; Peplow, M. A.; Pillai, J. Tetrahedron Lett. 1996, 37, 5825-5828.
27. (i) Quirante, J.; Escolano, C; Bonjoch, J. Synlett 1997, 179-180.
28. (j) Ref 1b.
29. Recent references: (a) Hanessian, S.; Ninkovic, S. J. Org. Chem. 1996, 61, 5418-5424.
30. (b) Della, E. W.; Knill, A. M. J. Org. Chem. 1996, 61, 7529-7533.
31. (c) Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1996, 52, 1069-1084.
32. (d) Goodall, K.; Parsons, A. F. Tetrahedron 1996, 52, 6739-6758.
33. (e) Andrés, C.; Duque-Soladana, J. P.; Iglesias, J. M.; Pedrosa, R. Tetrahedron Lett. 1996, 37, 9085-9086.
34. (f) Ref 1d.
35. (g) Bertrand, M. P.; Gastaldi, S.; Nouguier, R. Synlett 1997, 1420-1422.
36. (h) Parsons, A. F.; Pettifer, R. M. J. Chem. Soc., Perkin Trans. 1 1998, 651-660.
37. (i) Ikeda, M.; Teranishi, H.; Nozaki, K.; Ishibashi, H. J. Chem. Soc., Perkin Trans. 1 1998, 1691-1687.
38. (j) Giovannini, R.; Petrini, M. Synlett 1998, 90-92.
39. (k) El Kaim, L.; Gacon, A.; Perroux, A. Tetrahedron Lett. 1998, 39, 371-374.
40. (l) Gupta, V.; Besev, M.; Engman, L. Tetrahedron Lett. 1998, 39, 2429-2432.
41. (m) Baker, S. R.; Parsons, A. F.; Pons, J. F.; Wilson, M. Tetrahedron Lett. 1998, 39, 7197-7200.
42. Yuasa, Y.; Ando, J.; Shibuya, S. J. Chem. Soc., Perkin Trans. 1 1996, 793-802.
43. Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838-5839.
44. Generation of α-aminoalkyl radicals: (a) Murakami, M.; Hayashi, M.; Ito, Y. J. Org. Chem. 1992, 57. 793-794.
45. (b) Collin, J.; Namy, J. L.; Jones, G.; Kagan, H. B. Tetrahedron Lett. 1992, 33, 2973-2976.
46. (c) Schubert, S.; Renaud, P.; Carrupt, P. A.; Schenk, K. Helv. Chim. Acta 1993, 76, 2473-2489.
47. (d) Williams, L; Booth, S. E.; Undheim, K. Tetrahedron 1994, 50, 13697-13708.
48. (e) Santamaria, J. Pure Appl. Chem. 1995, 67, 141-147.
49. (f) Das, S.; Kumar, J. S. D.; Shivaramayya, K.; George, M. V. J. Chem. Soc., Perkin Trans. 1 1995, 1797-1799.
50. (g) Booth, S. E.; Benneche, T.; Undheim, K. Tetrahedron 1995, 51, 3665-3674.
51. (h) Khim, S. K.; Cederstrom, E.; Ferri, D. C.; Mariano, P. S. Tetrahedron 1996, 52, 3195-3222.
52. (i) Su, Z.; Falvey, D. E.; Yoon, U. C.; Mariano, P. S. J. Am. Chem. Soc. 1997, 119, 5261-5262.
53. (j) Ref 5h,i.
54. Padwa, A.; Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620-5627.
55. Padwa, A.; Dent, W.; Nimmesgern, H.; Venkatramanan, M. K.; Wong, G. S. K. Chem. Ber. 1986, 119, 813-828.
56. Recent reviews: (a) Molander, G. A. Chem. Rev. 1992, 92, 29-68.
57. (b) Molander, G. A. in Organic Reactions; Paquette, L. A. Ed.; John Wiley & Sons: New York, 1994; Vol. 46; pp 211-367.
58. (c) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338.
59. (d) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354.
60. Martin, S. F.; Yang, C. P.; Laswell, W. L.; Rüeger, H. Tetrahedron Lett. 1988, 29, 6685-6688.
61. (a) Aurrecoechea, J. M.; Fernández-Acebes, A. Tetrahedron Lett. 1992, 33, 4763-4766.
62. (b) Preliminary communication: Aurrecoechea, J. M.; Fernandez-Acebes, A. Synlett 1996, 39-42.
63. (c) Aurrecoechea, J. M.; López, B.; Fernández, A.; Arrieta, A.; Cossío, F. P. J. Org. Chem. 1997, 62, 1125-1135.
64. (d) Katritzky, A. R.; Qi, M.; Feng, D. M.; Nichols, D. A. J. Org. Chem. 1997, 62, 4121-4124.
65. (e) Katritzky, A. R.; Qi, M.; Feng, D. J. Org. Chem. 1998, 63, 6712-6714.
66. 2-mediated ring-closures see: (a) Ogawa, A.; Takami, N.; Sekiguchi, M.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 8729-8730.
67. (b) Shiue, J. S.; Fang, J. M. J. Chem. Soc., Chem. Commun. 1993, 1277-1278.
68. (c) Baldwin, J. E.; Mackenzieturner, S. C.; Moloney, M. G. Tetrahedron 1994, 50, 9411-9424.
69. (d) Baldwin, J. E.; Mackenzietunier, S. C.; Moloney, M. G. Tetrahedron 1994, 50, 9425-9438.
70. (e) Ha, D. C.; Yun, C. S.; Yu, E. Tetrahedron Lett. 1996, 37, 2577-2580.
71. For a recent synthesis of 2,5-substituted pyrrolidines using benzotriazole methodology see: Katritzky, A. R.; Cui, X. L.; Yang, B. Z.; Steel, P. J. Tetrahedron Lett. 1998, 39, 1697-1700.
72. Hirai, Y.; Terada, T.; Hagiwara, A.; Yamazaki, T. Chem. Pharm. Bull. 1988, 36, 1343-1350.
73. Brands, K. M. J.; Meekel. A. A. P.; Pandit, U. K. Tetrahedron 1991, 47, 2005-2026.
74. A recent review on benzotriazole synthetic applications: Katritzky, A. R.; Lan, X. F.; Yang, J. Z.; Denisko, O. V. Chem. Rev. 1998, 98, 409-548.
75. Katritzky, A. R.; Yannakopoulou, K.; Lue, P.; Rasala, D.; Urogdi, L. J. Chem. Soc., Perkin Trans. 1 1989, 225-233.
76. 2-promoted conjugate-additions has been recently illustrated: Molander, G. A.; Harris, C. R. J. Org. Chem. 1997, 62, 7418-7429.
77. For a related example, see Ref 14c.
78. Katritzky, A. R.; Yannakapoulou, K.; Kuzmierkiewicz, W.; Aurrecoechea, J. M.; Palenik, G. J.; Koziol, A. E.; Szczesniak, M.; Skarjune, R. J. Chem. Soc., Perkin Trans. 1 1987, 2673-2679.
79. 25 the rapid and irreversible reduction of the radical produced in a reversible α-amino radical cyclization: Katritzky, A. R.; Feng, D.; Qi, M.; Aurrecoechea, J. M.; Suero, R.; Aurrekoetxea, N. J. Org. Chem. 1999, submitted.
80. (a) Curran, D. P.; Totleben, M. J. J. Am. Chem. Soc. 1992, 114, 6050-6058.
81. (b) Hasegawa, E.; Curran, D. P. Tetrahedron Lett. 1993, 34, 1717-1720.
82. (a) Viehe, H. G.; Janousek, Z.; Merényi, R. Acc. Chem. Res. 1985, 18, 148-154.
83. (b) Sustmann, R.; Korth, H. G. Adv. Phys. Org. Chem. 1990, 26, 131-178.
84. (a) Yadav, V.; Fallis, A. G. Can. J. Chem. 1991, 69, 779-789.
85. (b) Whitesell, J. K.; Minton, M. A. Stereochemical Analysis of Alicyclic Compounds by C-13 NMR Spectroscopy, Chapman and Hall: London, 1987.
86. (a) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925-3941.
87. (b) Spellmeyer, D. C.; Houk, K. M. J. Org. Chem. 1987, 52, 959-974.
88. (c) Beckwith, A. L. J.; Zimmermann, J. J. Org. Chem. 1991, 56, 5791-5796.
89. (d) Beckwith, A. L. J. Chem. Soc. Rev. 1993, 22, 143-151.
90. Perrin, D. D.; Armarego, W. F. L. Purification of Laboratory Chemicals, 3rd Ed.; Pergamon Press: Oxford, 1988.
91. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.
92. Harwood, L. M. Aldrichimica Acta 1985, 18, 25.
93. Padwa, A.; Brodney, M. A.; Marino, J., J. P.; Sheehan, S. M. J. Org. Chem. 1997, 62, 78-87.
94. Ma, D.; Lu, X. Tetrahedron 1990, 46, 6319-6330.
95. Bosone, E.; Farina, P.; Guazzi, G.; Innocenti, S.; Marotta, V. Synthesis 1983, 942-944.
96. Optimized conditions for diamine 11b. Other attempts, under different conditions, led to lower yields of 11b and no cyclization.