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Volumn 70, Issue 2, 2005, Pages 681-683

Thiol-catalyzed acyl radical cyclization of alkenals

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; KETONES; OLEFINS; SUBSTITUTION REACTIONS;

EID: 12344334249     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048275a     Document Type: Article
Times cited : (76)

References (49)
  • 1
    • 0026418434 scopus 로고
    • Trost, B. M. Science 1991, 254, 1471-1477.
    • (1991) Science , vol.254 , pp. 1471-1477
    • Trost, B.M.1
  • 4
    • 0037430429 scopus 로고    scopus 로고
    • Our previous studies on the catalytic asymmetric Michael reaction of thiols: (a) Nishimura, K.; Tsubouchi, H.; Ono, M.; Hayama, T.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 2003, 44, 2323-2326. (b) Nishimura, K.; Tomioka, K. Yakugaku Zasshi 2003, 123, 9-18. (c) Nishimura, K.; Tomioka, K. J. Org. Chem. 2002, 67, 431-434. (d) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. Angew. Chem., Int. Ed. 2001, 40, 440-442. (e) Tomioka, K.; Okuda, M.; Nishimura, K.; Manabe, S.; Kanai, M.; Nagaoka, Y.; Koga, K. Tetrahedron Lett. 1998, 39, 2141-2144. (f) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 12974-12975. (g) Tomioka, K. Synthesis 1990, 541-549.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 2323-2326
    • Nishimura, K.1    Tsubouchi, H.2    Ono, M.3    Hayama, T.4    Nagaoka, Y.5    Tomioka, K.6
  • 5
    • 0037271986 scopus 로고    scopus 로고
    • Our previous studies on the catalytic asymmetric Michael reaction of thiols: (a) Nishimura, K.; Tsubouchi, H.; Ono, M.; Hayama, T.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 2003, 44, 2323-2326. (b) Nishimura, K.; Tomioka, K. Yakugaku Zasshi 2003, 123, 9-18. (c) Nishimura, K.; Tomioka, K. J. Org. Chem. 2002, 67, 431-434. (d) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. Angew. Chem., Int. Ed. 2001, 40, 440-442. (e) Tomioka, K.; Okuda, M.; Nishimura, K.; Manabe, S.; Kanai, M.; Nagaoka, Y.; Koga, K. Tetrahedron Lett. 1998, 39, 2141-2144. (f) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 12974-12975. (g) Tomioka, K. Synthesis 1990, 541-549.
    • (2003) Yakugaku Zasshi , vol.123 , pp. 9-18
    • Nishimura, K.1    Tomioka, K.2
  • 6
    • 0037169065 scopus 로고    scopus 로고
    • Our previous studies on the catalytic asymmetric Michael reaction of thiols: (a) Nishimura, K.; Tsubouchi, H.; Ono, M.; Hayama, T.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 2003, 44, 2323-2326. (b) Nishimura, K.; Tomioka, K. Yakugaku Zasshi 2003, 123, 9-18. (c) Nishimura, K.; Tomioka, K. J. Org. Chem. 2002, 67, 431-434. (d) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. Angew. Chem., Int. Ed. 2001, 40, 440-442. (e) Tomioka, K.; Okuda, M.; Nishimura, K.; Manabe, S.; Kanai, M.; Nagaoka, Y.; Koga, K. Tetrahedron Lett. 1998, 39, 2141-2144. (f) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 12974-12975. (g) Tomioka, K. Synthesis 1990, 541-549.
    • (2002) J. Org. Chem. , vol.67 , pp. 431-434
    • Nishimura, K.1    Tomioka, K.2
  • 7
    • 0035910477 scopus 로고    scopus 로고
    • Our previous studies on the catalytic asymmetric Michael reaction of thiols: (a) Nishimura, K.; Tsubouchi, H.; Ono, M.; Hayama, T.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 2003, 44, 2323-2326. (b) Nishimura, K.; Tomioka, K. Yakugaku Zasshi 2003, 123, 9-18. (c) Nishimura, K.; Tomioka, K. J. Org. Chem. 2002, 67, 431-434. (d) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. Angew. Chem., Int. Ed. 2001, 40, 440-442. (e) Tomioka, K.; Okuda, M.; Nishimura, K.; Manabe, S.; Kanai, M.; Nagaoka, Y.; Koga, K. Tetrahedron Lett. 1998, 39, 2141-2144. (f) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 12974-12975. (g) Tomioka, K. Synthesis 1990, 541-549.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 440-442
    • Nishimura, K.1    Ono, M.2    Nagaoka, Y.3    Tomioka, K.4
  • 8
    • 0032499028 scopus 로고    scopus 로고
    • Our previous studies on the catalytic asymmetric Michael reaction of thiols: (a) Nishimura, K.; Tsubouchi, H.; Ono, M.; Hayama, T.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 2003, 44, 2323-2326. (b) Nishimura, K.; Tomioka, K. Yakugaku Zasshi 2003, 123, 9-18. (c) Nishimura, K.; Tomioka, K. J. Org. Chem. 2002, 67, 431-434. (d) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. Angew. Chem., Int. Ed. 2001, 40, 440-442. (e) Tomioka, K.; Okuda, M.; Nishimura, K.; Manabe, S.; Kanai, M.; Nagaoka, Y.; Koga, K. Tetrahedron Lett. 1998, 39, 2141-2144. (f) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 12974-12975. (g) Tomioka, K. Synthesis 1990, 541-549.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 2141-2144
    • Tomioka, K.1    Okuda, M.2    Nishimura, K.3    Manabe, S.4    Kanai, M.5    Nagaoka, Y.6    Koga, K.7
  • 9
    • 0001314401 scopus 로고    scopus 로고
    • Our previous studies on the catalytic asymmetric Michael reaction of thiols: (a) Nishimura, K.; Tsubouchi, H.; Ono, M.; Hayama, T.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 2003, 44, 2323-2326. (b) Nishimura, K.; Tomioka, K. Yakugaku Zasshi 2003, 123, 9-18. (c) Nishimura, K.; Tomioka, K. J. Org. Chem. 2002, 67, 431-434. (d) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. Angew. Chem., Int. Ed. 2001, 40, 440-442. (e) Tomioka, K.; Okuda, M.; Nishimura, K.; Manabe, S.; Kanai, M.; Nagaoka, Y.; Koga, K. Tetrahedron Lett. 1998, 39, 2141-2144. (f) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 12974-12975. (g) Tomioka, K. Synthesis 1990, 541-549.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 12974-12975
    • Nishimura, K.1    Ono, M.2    Nagaoka, Y.3    Tomioka, K.4
  • 10
    • 0002991196 scopus 로고
    • Our previous studies on the catalytic asymmetric Michael reaction of thiols: (a) Nishimura, K.; Tsubouchi, H.; Ono, M.; Hayama, T.; Nagaoka, Y.; Tomioka, K. Tetrahedron Lett. 2003, 44, 2323-2326. (b) Nishimura, K.; Tomioka, K. Yakugaku Zasshi 2003, 123, 9-18. (c) Nishimura, K.; Tomioka, K. J. Org. Chem. 2002, 67, 431-434. (d) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. Angew. Chem., Int. Ed. 2001, 40, 440-442. (e) Tomioka, K.; Okuda, M.; Nishimura, K.; Manabe, S.; Kanai, M.; Nagaoka, Y.; Koga, K. Tetrahedron Lett. 1998, 39, 2141-2144. (f) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 12974-12975. (g) Tomioka, K. Synthesis 1990, 541-549.
    • (1990) Synthesis , pp. 541-549
    • Tomioka, K.1
  • 11
    • 0141539230 scopus 로고    scopus 로고
    • A dramatic inversion of cis/trans selectivity in a cyclization reaction was observed by changing an ionic reaction to a radical one: Denes, F.; Chemla, F.; Normant, J. F. Angew. Chem., Int. Ed. 2003, 42, 4043-4046.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 4043-4046
    • Denes, F.1    Chemla, F.2    Normant, J.F.3
  • 14
    • 0033484573 scopus 로고    scopus 로고
    • For polarity reversal catalysis of hydrogen atom abstraction: Roberts, B. P. Chem. Soc. Rev. 1999, 28, 25-35.
    • (1999) Chem. Soc. Rev. , vol.28 , pp. 25-35
    • Roberts, B.P.1
  • 29
    • 0142059744 scopus 로고    scopus 로고
    • A chiral carbene-catalyzed cyclization of this type: (a) Kerr, M. S.; Rovis, T. Synlett 2003, 1934-1936. (b) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299.
    • (2003) Synlett , pp. 1934-1936
    • Kerr, M.S.1    Rovis, T.2
  • 30
    • 0037019628 scopus 로고    scopus 로고
    • A chiral carbene-catalyzed cyclization of this type: (a) Kerr, M. S.; Rovis, T. Synlett 2003, 1934-1936. (b) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 10298-10299
    • Kerr, M.S.1    Read De Alaniz, J.2    Rovis, T.3
  • 32
    • 0037829795 scopus 로고    scopus 로고
    • Direct generation of an acyl radical and its intermolecular addition to an olefin: (a) Tsujimoto, S.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 2003, 44, 5601-5604. (b) Tsujimoto, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. Chem. Commun. 2001, 2352-2353. (c) Gottschalk, P.; Neckers, D. C. J. Org. Chem. 1985, 50, 3498-3502. See also ref 4.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 5601-5604
    • Tsujimoto, S.1    Sakaguchi, S.2    Ishii, Y.3
  • 33
    • 0035929999 scopus 로고    scopus 로고
    • Direct generation of an acyl radical and its intermolecular addition to an olefin: (a) Tsujimoto, S.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 2003, 44, 5601-5604. (b) Tsujimoto, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. Chem. Commun. 2001, 2352-2353. (c) Gottschalk, P.; Neckers, D. C. J. Org. Chem. 1985, 50, 3498-3502. See also ref 4.
    • (2001) Chem. Commun. , pp. 2352-2353
    • Tsujimoto, S.1    Iwahama, T.2    Sakaguchi, S.3    Ishii, Y.4
  • 34
    • 0000884797 scopus 로고
    • See also ref 4
    • Direct generation of an acyl radical and its intermolecular addition to an olefin: (a) Tsujimoto, S.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 2003, 44, 5601-5604. (b) Tsujimoto, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. Chem. Commun. 2001, 2352-2353. (c) Gottschalk, P.; Neckers, D. C. J. Org. Chem. 1985, 50, 3498-3502. See also ref 4.
    • (1985) J. Org. Chem. , vol.50 , pp. 3498-3502
    • Gottschalk, P.1    Neckers, D.C.2
  • 37
    • 12344258981 scopus 로고    scopus 로고
    • note
    • Under the standard argon atmosphere carboxylic acids were obtained along with 5a in poor yield.
  • 47
    • 0001823482 scopus 로고
    • Free Radical Additions to Olefins to Form Carbon-Carbon Bonds
    • Adams, R., Blatt, A. H., Boekelheide, V., Cairns, T. L., Cope, A. C., Curtin, D. Y., Niemann C., Eds.; Willey & Sons: New York
    • Walling, C.; Huyser, E. S. Free Radical Additions to Olefins to Form Carbon-Carbon Bonds. In Organic Reactions; Adams, R., Blatt, A. H., Boekelheide, V., Cairns, T. L., Cope, A. C., Curtin, D. Y., Niemann C., Eds.; Willey & Sons: New York, 1963; Vol. 13, pp 113-116.
    • (1963) Organic Reactions , vol.13 , pp. 113-116
    • Walling, C.1    Huyser, E.S.2
  • 48
    • 0037161769 scopus 로고    scopus 로고
    • The generation of acyl radicals from aldehydes via hydrogen abstraction by thiyl radicals and their reaction with a disulfide: Nambu, H.; Hata, K.; Matsugi, M.; Kita, Y. Chem. Commun. 2002, 1082-1083.
    • (2002) Chem. Commun. , pp. 1082-1083
    • Nambu, H.1    Hata, K.2    Matsugi, M.3    Kita, Y.4


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