메뉴 건너뛰기




Volumn 68, Issue 13, 2003, Pages 5139-5146

Triflic anhydride mediated cyclization of 5-hydroxy-substituted pyrrolidinones for the preparation of α-trifluoromethylsulfonamido furans

Author keywords

[No Author keywords available]

Indexed keywords

ANHYDROUS CONDITIONS;

EID: 0037534227     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0341970     Document Type: Article
Times cited : (31)

References (76)
  • 1
  • 9
    • 0001673091 scopus 로고
    • Trost, B. M., Ed.; Pergamon Press: New York
    • Hiemstra, H.; Speckamp, N. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 2, Part 2, pp 1047-1082.
    • (1991) Comprehensive Organic Synthesis , vol.2 , Issue.PART 2 , pp. 1047-1082
    • Hiemstra, H.1    Speckamp, N.2
  • 13
    • 46549103031 scopus 로고
    • Speckamp, W. N. Recl. Trav. Chim. Pays-Bas 1981, 100, 345. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
    • (1985) Tetrahedron , vol.41 , pp. 4367
    • Speckamp, W.N.1    Hiemstra, H.2
  • 26
  • 27
    • 0027940177 scopus 로고
    • Bailey, P. D.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. Tetrahedron Lett. 1994, 35, 7115. De Koning, H.; Speckamp, W. N. In Houben-Weyl, Methods in Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, Germany, 1995; Vol. E21b, pp 1953-2009.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 7115
    • Bailey, P.D.1    Morgan, K.M.2    Smith, D.I.3    Vernon, J.M.4
  • 28
    • 0000188393 scopus 로고
    • Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, Germany
    • Bailey, P. D.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. Tetrahedron Lett. 1994, 35, 7115. De Koning, H.; Speckamp, W. N. In Houben-Weyl, Methods in Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, Germany, 1995; Vol. E21b, pp 1953-2009.
    • (1995) Houben-Weyl, Methods in Organic Chemistry , vol.E21B , pp. 1953-2009
    • De Koning, H.1    Speckampv, W.N.2
  • 29
    • 0035479706 scopus 로고    scopus 로고
    • Santos, L. S.; Pilli, R. A. Tetrahedron Lett. 2001, 42, 6999. Pilli, R. A.; Zanotto, P. A.; Böckelmann, M. A. Tetrahedron Lett. 2001, 42, 7003.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 6999
    • Santos, L.S.1    Pilli, R.A.2
  • 31
    • 0032572861 scopus 로고    scopus 로고
    • Aoyagi, Y.; Williams, R. M. Tetrahedron 1998, 54, 10419. Keum, G.; Kim, G. Bull. Korean Chem. Soc. 1994, 15, 278. Martin, S. F.; Bur, S. K. Tetrahedron Lett. 1997, 38, 7641.
    • (1998) Tetrahedron , vol.54 , pp. 10419
    • Aoyagi, Y.1    Williams, R.M.2
  • 32
    • 0013273995 scopus 로고
    • Aoyagi, Y.; Williams, R. M. Tetrahedron 1998, 54, 10419. Keum, G.; Kim, G. Bull. Korean Chem. Soc. 1994, 15, 278. Martin, S. F.; Bur, S. K. Tetrahedron Lett. 1997, 38, 7641.
    • (1994) Bull. Korean Chem. Soc. , vol.15 , pp. 278
    • Keum, G.1    Kim, G.2
  • 33
    • 0030694005 scopus 로고    scopus 로고
    • Aoyagi, Y.; Williams, R. M. Tetrahedron 1998, 54, 10419. Keum, G.; Kim, G. Bull. Korean Chem. Soc. 1994, 15, 278. Martin, S. F.; Bur, S. K. Tetrahedron Lett. 1997, 38, 7641.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 7641
    • Martin, S.F.1    Bur, S.K.2
  • 35
    • 0034609701 scopus 로고    scopus 로고
    • Padwa, A.; Dimitroff, M.; Liu, B. Org. Lett. 2000, 2, 3233. Padwa, A.; Brodney, M. A.; Lynch, S. M. J. Org. Chem. 2001, 66, 1716. Ginn, J. D.; Padwa, A. Org. Lett. 2002, 4, 1515.
    • (2000) Org. Lett. , vol.2 , pp. 3233
    • Padwa, A.1    Dimitroff, M.2    Liu, B.3
  • 36
    • 0035831159 scopus 로고    scopus 로고
    • Padwa, A.; Dimitroff, M.; Liu, B. Org. Lett. 2000, 2, 3233. Padwa, A.; Brodney, M. A.; Lynch, S. M. J. Org. Chem. 2001, 66, 1716. Ginn, J. D.; Padwa, A. Org. Lett. 2002, 4, 1515.
    • (2001) J. Org. Chem. , vol.66 , pp. 1716
    • Padwa, A.1    Brodney, M.A.2    Lynch, S.M.3
  • 37
    • 0037007716 scopus 로고    scopus 로고
    • Padwa, A.; Dimitroff, M.; Liu, B. Org. Lett. 2000, 2, 3233. Padwa, A.; Brodney, M. A.; Lynch, S. M. J. Org. Chem. 2001, 66, 1716. Ginn, J. D.; Padwa, A. Org. Lett. 2002, 4, 1515.
    • (2002) Org. Lett. , vol.4 , pp. 1515
    • Ginn, J.D.1    Padwa, A.2
  • 40
    • 0038032286 scopus 로고
    • For some reviews dealing with triflic anhydride, see: Ritter, K. Synthesis 1993, 735. Stang, P. J.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85. Braznenok, I. L.; Nenajjdenko, V. G.; Balenkova, E. S. Tetrahedron 2000, 56, 3077.
    • (1993) Synthesis , vol.735
    • Ritter, K.1
  • 41
    • 85007950754 scopus 로고
    • For some reviews dealing with triflic anhydride, see: Ritter, K. Synthesis 1993, 735. Stang, P. J.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85. Braznenok, I. L.; Nenajjdenko, V. G.; Balenkova, E. S. Tetrahedron 2000, 56, 3077.
    • (1982) Synthesis , pp. 85
    • Stang, P.J.1    Hanack, M.2    Subramanian, L.R.3
  • 42
    • 0034640532 scopus 로고    scopus 로고
    • For some reviews dealing with triflic anhydride, see: Ritter, K. Synthesis 1993, 735. Stang, P. J.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85. Braznenok, I. L.; Nenajjdenko, V. G.; Balenkova, E. S. Tetrahedron 2000, 56, 3077.
    • (2000) Tetrahedron , vol.56 , pp. 3077
    • Braznenok, I.L.1    Nenajjdenko, V.G.2    Balenkova, E.S.3
  • 43
    • 0030668491 scopus 로고    scopus 로고
    • Charette, A. B.; Chua, P. Tetrahedron Lett. 1997, 38, 1997. Charette, A. B.; Chua, P. Tetrahedron Lett. 1997, 38, 8499. Charette, A. B.; Chua, P. Tetrahedron Lett. 1998, 39, 245. Charette, A. B.; Chua, P. J. Org. Chem. 1998, 63, 908. Charette, A. B.; Chua, P. Synlett 1998, 163. Charette, A. B.; Grenon, M. Tetrahedron Lett. 2000, 41, 1677.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 1997
    • Charette, A.B.1    Chua, P.2
  • 44
    • 0030668491 scopus 로고    scopus 로고
    • Charette, A. B.; Chua, P. Tetrahedron Lett. 1997, 38, 1997. Charette, A. B.; Chua, P. Tetrahedron Lett. 1997, 38, 8499. Charette, A. B.; Chua, P. Tetrahedron Lett. 1998, 39, 245. Charette, A. B.; Chua, P. J. Org. Chem. 1998, 63, 908. Charette, A. B.; Chua, P. Synlett 1998, 163. Charette, A. B.; Grenon, M. Tetrahedron Lett. 2000, 41, 1677.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 8499
    • Charette, A.B.1    Chua, P.2
  • 45
    • 0032518886 scopus 로고    scopus 로고
    • Charette, A. B.; Chua, P. Tetrahedron Lett. 1997, 38, 1997. Charette, A. B.; Chua, P. Tetrahedron Lett. 1997, 38, 8499. Charette, A. B.; Chua, P. Tetrahedron Lett. 1998, 39, 245. Charette, A. B.; Chua, P. J. Org. Chem. 1998, 63, 908. Charette, A. B.; Chua, P. Synlett 1998, 163. Charette, A. B.; Grenon, M. Tetrahedron Lett. 2000, 41, 1677.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 245
    • Charette, A.B.1    Chua, P.2
  • 46
    • 0001004124 scopus 로고    scopus 로고
    • Charette, A. B.; Chua, P. Tetrahedron Lett. 1997, 38, 1997. Charette, A. B.; Chua, P. Tetrahedron Lett. 1997, 38, 8499. Charette, A. B.; Chua, P. Tetrahedron Lett. 1998, 39, 245. Charette, A. B.; Chua, P. J. Org. Chem. 1998, 63, 908. Charette, A. B.; Chua, P. Synlett 1998, 163. Charette, A. B.; Grenon, M. Tetrahedron Lett. 2000, 41, 1677.
    • (1998) J. Org. Chem. , vol.63 , pp. 908
    • Charette, A.B.1    Chua, P.2
  • 47
    • 0038032278 scopus 로고    scopus 로고
    • Charette, A. B.; Chua, P. Tetrahedron Lett. 1997, 38, 1997. Charette, A. B.; Chua, P. Tetrahedron Lett. 1997, 38, 8499. Charette, A. B.; Chua, P. Tetrahedron Lett. 1998, 39, 245. Charette, A. B.; Chua, P. J. Org. Chem. 1998, 63, 908. Charette, A. B.; Chua, P. Synlett 1998, 163. Charette, A. B.; Grenon, M. Tetrahedron Lett. 2000, 41, 1677.
    • (1998) Synlett , vol.163
    • Charette, A.B.1    Chua, P.2
  • 48
    • 0034635862 scopus 로고    scopus 로고
    • Charette, A. B.; Chua, P. Tetrahedron Lett. 1997, 38, 1997. Charette, A. B.; Chua, P. Tetrahedron Lett. 1997, 38, 8499. Charette, A. B.; Chua, P. Tetrahedron Lett. 1998, 39, 245. Charette, A. B.; Chua, P. J. Org. Chem. 1998, 63, 908. Charette, A. B.; Chua, P. Synlett 1998, 163. Charette, A. B.; Grenon, M. Tetrahedron Lett. 2000, 41, 1677.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 1677
    • Charette, A.B.1    Grenon, M.2
  • 51
    • 84918218889 scopus 로고
    • Sisti, N. J.; Fowler, F. W.; Grierson, D. S. Synlett 1991, 816. Sisti, N. J.; Zeller, E.; Grierson, D. S.; Fowler, F. W. J. Org. Chem. 1997, 62, 2093. Thomas, E. W. Synthesis 1993, 767.
    • (1991) Synlett , pp. 816
    • Sisti, N.J.1    Fowler, F.W.2    Grierson, D.S.3
  • 53
    • 0027209127 scopus 로고
    • Sisti, N. J.; Fowler, F. W.; Grierson, D. S. Synlett 1991, 816. Sisti, N. J.; Zeller, E.; Grierson, D. S.; Fowler, F. W. J. Org. Chem. 1997, 62, 2093. Thomas, E. W. Synthesis 1993, 767.
    • (1993) Synthesis , pp. 767
    • Thomas, E.W.1
  • 54
    • 0001150689 scopus 로고
    • Szantay, C. Pure Appl. Chem. 1990, 62, 1299. Hibino, S.; Choshi, T. Nat. Prod. Rep. 2002, 19, 148 and earlier reviews in the series.
    • (1990) Pure Appl. Chem. , vol.62 , pp. 1299
    • Szantay, C.1
  • 55
    • 0036005604 scopus 로고    scopus 로고
    • Szantay, C. Pure Appl. Chem. 1990, 62, 1299. Hibino, S.; Choshi, T. Nat. Prod. Rep. 2002, 19, 148 and earlier reviews in the series.
    • (2002) Nat. Prod. Rep. , vol.19 , pp. 148
    • Hibino, S.1    Choshi, T.2
  • 56
    • 8044234029 scopus 로고
    • Alvarez, M.; Salas, M.; Joule, J. A. Heterocycles 1991, 32, 1391. Black, D. S. C. Synlett 1993, 246. Hughes, D. L. Org. Prep. Proc. Int. 1993, 25, 607.
    • (1991) Heterocycles , vol.32 , pp. 1391
    • Alvarez, M.1    Salas, M.2    Joule, J.A.3
  • 57
    • 85032668744 scopus 로고
    • Alvarez, M.; Salas, M.; Joule, J. A. Heterocycles 1991, 32, 1391. Black, D. S. C. Synlett 1993, 246. Hughes, D. L. Org. Prep. Proc. Int. 1993, 25, 607.
    • (1993) Synlett , pp. 246
    • Black, D.S.C.1
  • 58
    • 40749104841 scopus 로고
    • Alvarez, M.; Salas, M.; Joule, J. A. Heterocycles 1991, 32, 1391. Black, D. S. C. Synlett 1993, 246. Hughes, D. L. Org. Prep. Proc. Int. 1993, 25, 607.
    • (1993) Org. Prep. Proc. Int. , vol.25 , pp. 607
    • Hughes, D.L.1
  • 60
    • 0037037841 scopus 로고    scopus 로고
    • Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. Crawford, K. R.; Padwa, A. Tetrahedron Lett. 2002, 43, 7365.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 7365
    • Crawford, K.R.1    Padwa, A.2
  • 62
    • 0030845835 scopus 로고    scopus 로고
    • Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179. Sternbach, D. D.; Rossana, D. M.; Onon, K. D. J. Org. Chem. 1984, 49, 3427. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1989, 111, 5469.
    • (1997) Tetrahedron , vol.53 , pp. 14179
    • Kappe, C.O.1    Murphree, S.S.2    Padwa, A.3
  • 63
    • 0001549912 scopus 로고
    • Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179. Sternbach, D. D.; Rossana, D. M.; Onon, K. D. J. Org. Chem. 1984, 49, 3427. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1989, 111, 5469.
    • (1984) J. Org. Chem. , vol.49 , pp. 3427
    • Sternbach, D.D.1    Rossana, D.M.2    Onon, K.D.3
  • 64
    • 0001318394 scopus 로고
    • Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179. Sternbach, D. D.; Rossana, D. M.; Onon, K. D. J. Org. Chem. 1984, 49, 3427. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1989, 111, 5469.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 5469
    • Jung, M.E.1    Gervay, J.2
  • 65
    • 0028017556 scopus 로고
    • Woo, S.; Keay, B. Tetrahedron: Asymmetry 1994, 5, 1411. Rogers, C.; Keay, B. A. Tetrahedron Lett. 1991, 32, 6477. Rogers, C.; Keay, B. A. Can. J. Chem. 1992, 70, 2929. De Clercq, P. J.; Van Royen, L. A. Synth. Commun. 1979, 9, 771. Fischer, K.; Hunig, S. J. Org. Chem. 1987, 52, 564.
    • (1994) Tetrahedron: Asymmetry , vol.5 , pp. 1411
    • Woo, S.1    Keay, B.2
  • 66
    • 0025995752 scopus 로고
    • Woo, S.; Keay, B. Tetrahedron: Asymmetry 1994, 5, 1411. Rogers, C.; Keay, B. A. Tetrahedron Lett. 1991, 32, 6477. Rogers, C.; Keay, B. A. Can. J. Chem. 1992, 70, 2929. De Clercq, P. J.; Van Royen, L. A. Synth. Commun. 1979, 9, 771. Fischer, K.; Hunig, S. J. Org. Chem. 1987, 52, 564.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 6477
    • Rogers, C.1    Keay, B.A.2
  • 67
    • 0000780402 scopus 로고
    • Woo, S.; Keay, B. Tetrahedron: Asymmetry 1994, 5, 1411. Rogers, C.; Keay, B. A. Tetrahedron Lett. 1991, 32, 6477. Rogers, C.; Keay, B. A. Can. J. Chem. 1992, 70, 2929. De Clercq, P. J.; Van Royen, L. A. Synth. Commun. 1979, 9, 771. Fischer, K.; Hunig, S. J. Org. Chem. 1987, 52, 564.
    • (1992) Can. J. Chem. , vol.70 , pp. 2929
    • Rogers, C.1    Keay, B.A.2
  • 68
    • 0343758072 scopus 로고
    • Woo, S.; Keay, B. Tetrahedron: Asymmetry 1994, 5, 1411. Rogers, C.; Keay, B. A. Tetrahedron Lett. 1991, 32, 6477. Rogers, C.; Keay, B. A. Can. J. Chem. 1992, 70, 2929. De Clercq, P. J.; Van Royen, L. A. Synth. Commun. 1979, 9, 771. Fischer, K.; Hunig, S. J. Org. Chem. 1987, 52, 564.
    • (1979) Synth. Commun. , vol.9 , pp. 771
    • De Clercq, P.J.1    Van Royen, L.A.2
  • 69
    • 0000496674 scopus 로고
    • Woo, S.; Keay, B. Tetrahedron: Asymmetry 1994, 5, 1411. Rogers, C.; Keay, B. A. Tetrahedron Lett. 1991, 32, 6477. Rogers, C.; Keay, B. A. Can. J. Chem. 1992, 70, 2929. De Clercq, P. J.; Van Royen, L. A. Synth. Commun. 1979, 9, 771. Fischer, K.; Hunig, S. J. Org. Chem. 1987, 52, 564.
    • (1987) J. Org. Chem. , vol.52 , pp. 564
    • Fischer, K.1    Hunig, S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.