Pyrrolidines from β-Aminoselenides via Radical Cyclization. Diastereoselectivity Control by the N-Substituent

Organic Letters

Volumn 2, Issue 11, 2000, Pages 1589-1592

  Besev, Magnus ^a   Engman, Lars ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000883788     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005829x     Document Type: Article

References (61)

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42. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poll, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenard-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
43. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poll, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenard-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
44. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poll, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenard-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
45. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poll, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenard-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
46. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poll, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenard-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
47. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poll, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenard-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
48. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poll, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenard-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
49. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poll, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenard-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
50. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poll, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenard-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
51. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poll, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenard-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
52. For examples of 3-aza-5-hexenyl radical cyclizations of varying diastereoselectivity, see: Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4273. Andrés, C.; Duque-Soladana, J. P.; Pedrosa, R. J. Org. Chem. 1999, 64, 4282. Bertrand, M.-P.; Gastaldi, S.; Nouguier, R. Tetrahedron 1998, 54, 12829. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871. Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977. Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassallo, M. Tetrahedron 1992, 48, 3945. Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1992, 48, 9373. Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1 1991, 2885. Gennari, C.; Poll, G.; Scolastico, C.; Vassallo, M. Tetrahedron: Asymmetry 1991, 2, 793. Bachi, M. D.; De Mesmaeker, A.; Stevenard-De Mesmaeker, N. Tetrahedron Lett. 1987, 28, 2637. Watanabe, Y.; Ueno, Y.; Tanaka, C.; Okawara, M.; Endo, T. Tetrahedron Lett. 1987, 28, 3953.
53. Gupta, V.; Besev, M.; Engman, L. Tetrahedron Lett. 1998, 39, 2429.
54. Nagashima, H.; Ozaki, N.; Ishii, M.; Seki, K.; Washiyama, M.; Itoh, K. J. Org. Chem. 1993, 58, 464.
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56. Engman, L. J. Org. Chem. 1988, 53, 4031. Engman, L. Tetrahedron Lett. 1985, 26, 6385.
57. White, W. A.; Weingarten, H. J. Am. Chem. Soc. 1967, 32, 213.
58. For literature precedent describing the preferred axial disposition of a C-2 alkyl substituent in N-protected piperidine systems, see: Craig, D.; Meadows, J. D.; Pécheux, M.; Tetrahedron Lett. 1998, 39, 147. Hopman, J. C. P.; van den Berg, E.; Ollero Ollero, L.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1995, 36, 4315. Brown, J. D.; Foley, M. A.; Comins, D. L. J. Am. Chem. Soc. 1988, 110, 7445.
59. For literature precedent describing the preferred axial disposition of a C-2 alkyl substituent in N-protected piperidine systems, see: Craig, D.; Meadows, J. D.; Pécheux, M.; Tetrahedron Lett. 1998, 39, 147. Hopman, J. C. P.; van den Berg, E.; Ollero Ollero, L.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1995, 36, 4315. Brown, J. D.; Foley, M. A.; Comins, D. L. J. Am. Chem. Soc. 1988, 110, 7445.
60. For literature precedent describing the preferred axial disposition of a C-2 alkyl substituent in N-protected piperidine systems, see: Craig, D.; Meadows, J. D.; Pécheux, M.; Tetrahedron Lett. 1998, 39, 147. Hopman, J. C. P.; van den Berg, E.; Ollero Ollero, L.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1995, 36, 4315. Brown, J. D.; Foley, M. A.; Comins, D. L. J. Am. Chem. Soc. 1988, 110, 7445.
61. Attempts to use triethylborane as an initiator at ambient temperature were unsuccessful.