Highly Diastereoselective Intermolecular β-Addition of Alkyl Radicals to Chiral 2-(Arylsulfinyl)-2-cycloalkenones

Journal of Organic Chemistry

Volumn 62, Issue 22, 1997, Pages 7794-7800

  Mase, Nobuyuki ^a   Watanabe, Yoshihiko ^a   Ueno, Yoshio ^a   Toru, Takeshi ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000456131     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971093e     Document Type: Article

References (67)

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54. There are several reports on the stereoselective formation of both diastereoisomers depending on the conditions with or without Lewis acids in the radical 1,2-asymmetric inductions, see: (a) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 5 (2), 190. (b) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090. (c) Gerster, M.; Audergon, L.; Moufid, N.; Renaud, P. Tetrahedron Lett. 1996, 37 (35), 6335. (d) Nagano, H.; Kuno, Y.; Omori, Y.; Iguchi, M. J. Chem. Soc., Perkin Trans. 1 1995, 389. (e) Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett 1995, 449. (f) Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1601. (g) Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421.
55. There are several reports on the stereoselective formation of both diastereoisomers depending on the conditions with or without Lewis acids in the radical 1,2-asymmetric inductions, see: (a) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 5 (2), 190. (b) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090. (c) Gerster, M.; Audergon, L.; Moufid, N.; Renaud, P. Tetrahedron Lett. 1996, 37 (35), 6335. (d) Nagano, H.; Kuno, Y.; Omori, Y.; Iguchi, M. J. Chem. Soc., Perkin Trans. 1 1995, 389. (e) Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett 1995, 449. (f) Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1601. (g) Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421.
56. There are several reports on the stereoselective formation of both diastereoisomers depending on the conditions with or without Lewis acids in the radical 1,2-asymmetric inductions, see: (a) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 5 (2), 190. (b) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090. (c) Gerster, M.; Audergon, L.; Moufid, N.; Renaud, P. Tetrahedron Lett. 1996, 37 (35), 6335. (d) Nagano, H.; Kuno, Y.; Omori, Y.; Iguchi, M. J. Chem. Soc., Perkin Trans. 1 1995, 389. (e) Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett 1995, 449. (f) Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1601. (g) Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421.
57. There are several reports on the stereoselective formation of both diastereoisomers depending on the conditions with or without Lewis acids in the radical 1,2-asymmetric inductions, see: (a) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 5 (2), 190. (b) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090. (c) Gerster, M.; Audergon, L.; Moufid, N.; Renaud, P. Tetrahedron Lett. 1996, 37 (35), 6335. (d) Nagano, H.; Kuno, Y.; Omori, Y.; Iguchi, M. J. Chem. Soc., Perkin Trans. 1 1995, 389. (e) Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett 1995, 449. (f) Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1601. (g) Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421.
58. There are several reports on the stereoselective formation of both diastereoisomers depending on the conditions with or without Lewis acids in the radical 1,2-asymmetric inductions, see: (a) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 5 (2), 190. (b) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090. (c) Gerster, M.; Audergon, L.; Moufid, N.; Renaud, P. Tetrahedron Lett. 1996, 37 (35), 6335. (d) Nagano, H.; Kuno, Y.; Omori, Y.; Iguchi, M. J. Chem. Soc., Perkin Trans. 1 1995, 389. (e) Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett 1995, 449. (f) Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1601. (g) Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421.
59. There are several reports on the stereoselective formation of both diastereoisomers depending on the conditions with or without Lewis acids in the radical 1,2-asymmetric inductions, see: (a) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 5 (2), 190. (b) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090. (c) Gerster, M.; Audergon, L.; Moufid, N.; Renaud, P. Tetrahedron Lett. 1996, 37 (35), 6335. (d) Nagano, H.; Kuno, Y.; Omori, Y.; Iguchi, M. J. Chem. Soc., Perkin Trans. 1 1995, 389. (e) Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett 1995, 449. (f) Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1601. (g) Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421.
60. There are several reports on the stereoselective formation of both diastereoisomers depending on the conditions with or without Lewis acids in the radical 1,2-asymmetric inductions, see: (a) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 5 (2), 190. (b) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090. (c) Gerster, M.; Audergon, L.; Moufid, N.; Renaud, P. Tetrahedron Lett. 1996, 37 (35), 6335. (d) Nagano, H.; Kuno, Y.; Omori, Y.; Iguchi, M. J. Chem. Soc., Perkin Trans. 1 1995, 389. (e) Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Synlett 1995, 449. (f) Renaud, P.; Bourquard, T.; Gerster, M.; Moufid, N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1601. (g) Yamamoto, Y.; Onuki, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421.
61. (a) For 3-ethyl-2-cyclopentanone, see ref 7.
62. (b) For 3-isopropyl-2-cyclopentanone, see ref 7 and references therein.
63. (c) For 3-cyclohexyl-2-cyclopentanone, see: Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 116, 1821 and references therein.
64. (d) For 3-tert-butyl-2-cyclopentanone, see: Tichy, M.; Malon, P.; Fric, I.; Blaha, K. Collect. Czech. Chem. Commun. 1977, 42, 3591.
65. (e) For 3-isopropyl-2-cyclohexanone, see, ref 7.
66. (a) Alexakis, A.; Frutos, J. C.; Mangeney, P. Tetrahedron: Asymmetry 1993, 4 (12), 2431.
67. (b) Lemière, G. L.; Dommisse, R. A.; Lepoivre, J. A.; Alderweireldt, F. C.; Hiemstra, H.; Wynberg, H.; Jones, J. B.; Toone, E. J. J. Am. Chem. Soc. 1987, 109, 1363.