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Volumn 340, Issue 1, 1998, Pages 1-10

Sultones in Organic Synthesis

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EID: 2742605030     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review
Times cited : (23)

References (71)
  • 2
    • 0001411520 scopus 로고
    • For reviews of sultone chemistry, see: (a) A. J. Buglass, J. G. Tillett, The Chemistry of Sulphonic Acids, Esters and their Derivatives, S. Patai, Z. Rappoport, eds., Wiley, New York 1991, p. 798; (b) D. W. Roberts, D. L. Williams, Tetrahedron 43 (1987) 1027
    • (1987) Tetrahedron , vol.43 , pp. 1027
    • Roberts, D.W.1    Williams, D.L.2
  • 3
    • 0026730266 scopus 로고    scopus 로고
    • For more recent studies on sultones by other groups, see: (a) M. J. Perez-Perez, J. Balzarini, M. Hosova, E. De Clercq, M. J. Camarasa, Bioorg. Med. Chem. Lett. 2 (1992) 647; (b) W. B. Motherwell, A. M. K. Pennell, F. Ujjainwalla, J. Chem. Soc., Chem. Commun. 1992, 1067; (c) P. A. Crooks, R. C. Reynolds, J. A. Maddry, A. Rathore, M. S. Akhtar, J. A. Montgomery, J. A. I. Secrist, J. Org. Chem. 57 (1992) 2830; (d) N. Asao, M. Meguro, Y. Yamamoto, Synlett 1994, 185; (e) N. De Kimpe, M. Boeykens, L. Lazar, Z. Szakonyi, A. Kemme, G. Duburs, Bull. Soc. Chim. Belg. 103 (1994) 299; (f) G. Galley, M. Pätzel, J. Chem. Soc., Perkin Trans. 1 1996, 2297; (g) A. W. M. Lee, W. H. Chan, Top. Curr. Chem. 190 (1997) 103; (h) S. Doye, T. Hotopp, E. Winterfeldt, Chem. Commun. 1997, 1491
    • (1992) Bioorg. Med. Chem. Lett. , vol.2 , pp. 647
    • Perez-Perez, M.J.1    Balzarini, J.2    Hosova, M.3    De Clercq, E.4    Camarasa, M.J.5
  • 4
    • 37049086095 scopus 로고    scopus 로고
    • For more recent studies on sultones by other groups, see: (a) M. J. Perez-Perez, J. Balzarini, M. Hosova, E. De Clercq, M. J. Camarasa, Bioorg. Med. Chem. Lett. 2 (1992) 647; (b) W. B. Motherwell, A. M. K. Pennell, F. Ujjainwalla, J. Chem. Soc., Chem. Commun. 1992, 1067; (c) P. A. Crooks, R. C. Reynolds, J. A. Maddry, A. Rathore, M. S. Akhtar, J. A. Montgomery, J. A. I. Secrist, J. Org. Chem. 57 (1992) 2830; (d) N. Asao, M. Meguro, Y. Yamamoto, Synlett 1994, 185; (e) N. De Kimpe, M. Boeykens, L. Lazar, Z. Szakonyi, A. Kemme, G. Duburs, Bull. Soc. Chim. Belg. 103 (1994) 299; (f) G. Galley, M. Pätzel, J. Chem. Soc., Perkin Trans. 1 1996, 2297; (g) A. W. M. Lee, W. H. Chan, Top. Curr. Chem. 190 (1997) 103; (h) S. Doye, T. Hotopp, E. Winterfeldt, Chem. Commun. 1997, 1491
    • J. Chem. Soc., Chem. Commun. , vol.1992 , pp. 1067
    • Motherwell, W.B.1    Pennell, A.M.K.2    Ujjainwalla, F.3
  • 5
    • 0026648023 scopus 로고
    • For more recent studies on sultones by other groups, see: (a) M. J. Perez-Perez, J. Balzarini, M. Hosova, E. De Clercq, M. J. Camarasa, Bioorg. Med. Chem. Lett. 2 (1992) 647; (b) W. B. Motherwell, A. M. K. Pennell, F. Ujjainwalla, J. Chem. Soc., Chem. Commun. 1992, 1067; (c) P. A. Crooks, R. C. Reynolds, J. A. Maddry, A. Rathore, M. S. Akhtar, J. A. Montgomery, J. A. I. Secrist, J. Org. Chem. 57 (1992) 2830; (d) N. Asao, M. Meguro, Y. Yamamoto, Synlett 1994, 185; (e) N. De Kimpe, M. Boeykens, L. Lazar, Z. Szakonyi, A. Kemme, G. Duburs, Bull. Soc. Chim. Belg. 103 (1994) 299; (f) G. Galley, M. Pätzel, J. Chem. Soc., Perkin Trans. 1 1996, 2297; (g) A. W. M. Lee, W. H. Chan, Top. Curr. Chem. 190 (1997) 103; (h) S. Doye, T. Hotopp, E. Winterfeldt, Chem. Commun. 1997, 1491
    • (1992) J. Org. Chem. , vol.57 , pp. 2830
    • Crooks, P.A.1    Reynolds, R.C.2    Maddry, J.A.3    Rathore, A.4    Akhtar, M.S.5    Montgomery, J.A.6    Secrist, J.A.I.7
  • 6
    • 2742609689 scopus 로고    scopus 로고
    • For more recent studies on sultones by other groups, see: (a) M. J. Perez-Perez, J. Balzarini, M. Hosova, E. De Clercq, M. J. Camarasa, Bioorg. Med. Chem. Lett. 2 (1992) 647; (b) W. B. Motherwell, A. M. K. Pennell, F. Ujjainwalla, J. Chem. Soc., Chem. Commun. 1992, 1067; (c) P. A. Crooks, R. C. Reynolds, J. A. Maddry, A. Rathore, M. S. Akhtar, J. A. Montgomery, J. A. I. Secrist, J. Org. Chem. 57 (1992) 2830; (d) N. Asao, M. Meguro, Y. Yamamoto, Synlett 1994, 185; (e) N. De Kimpe, M. Boeykens, L. Lazar, Z. Szakonyi, A. Kemme, G. Duburs, Bull. Soc. Chim. Belg. 103 (1994) 299; (f) G. Galley, M. Pätzel, J. Chem. Soc., Perkin Trans. 1 1996, 2297; (g) A. W. M. Lee, W. H. Chan, Top. Curr. Chem. 190 (1997) 103; (h) S. Doye, T. Hotopp, E. Winterfeldt, Chem. Commun. 1997, 1491
    • Synlett , vol.1994 , pp. 185
    • Asao, N.1    Meguro, M.2    Yamamoto, Y.3
  • 7
    • 84988128695 scopus 로고
    • For more recent studies on sultones by other groups, see: (a) M. J. Perez-Perez, J. Balzarini, M. Hosova, E. De Clercq, M. J. Camarasa, Bioorg. Med. Chem. Lett. 2 (1992) 647; (b) W. B. Motherwell, A. M. K. Pennell, F. Ujjainwalla, J. Chem. Soc., Chem. Commun. 1992, 1067; (c) P. A. Crooks, R. C. Reynolds, J. A. Maddry, A. Rathore, M. S. Akhtar, J. A. Montgomery, J. A. I. Secrist, J. Org. Chem. 57 (1992) 2830; (d) N. Asao, M. Meguro, Y. Yamamoto, Synlett 1994, 185; (e) N. De Kimpe, M. Boeykens, L. Lazar, Z. Szakonyi, A. Kemme, G. Duburs, Bull. Soc. Chim. Belg. 103 (1994) 299; (f) G. Galley, M. Pätzel, J. Chem. Soc., Perkin Trans. 1 1996, 2297; (g) A. W. M. Lee, W. H. Chan, Top. Curr. Chem. 190 (1997) 103; (h) S. Doye, T. Hotopp, E. Winterfeldt, Chem. Commun. 1997, 1491
    • (1994) Bull. Soc. Chim. Belg. , vol.103 , pp. 299
    • De Kimpe, N.1    Boeykens, M.2    Lazar, L.3    Szakonyi, Z.4    Kemme, A.5    Duburs, G.6
  • 8
    • 33749142104 scopus 로고    scopus 로고
    • For more recent studies on sultones by other groups, see: (a) M. J. Perez-Perez, J. Balzarini, M. Hosova, E. De Clercq, M. J. Camarasa, Bioorg. Med. Chem. Lett. 2 (1992) 647; (b) W. B. Motherwell, A. M. K. Pennell, F. Ujjainwalla, J. Chem. Soc., Chem. Commun. 1992, 1067; (c) P. A. Crooks, R. C. Reynolds, J. A. Maddry, A. Rathore, M. S. Akhtar, J. A. Montgomery, J. A. I. Secrist, J. Org. Chem. 57 (1992) 2830; (d) N. Asao, M. Meguro, Y. Yamamoto, Synlett 1994, 185; (e) N. De Kimpe, M. Boeykens, L. Lazar, Z. Szakonyi, A. Kemme, G. Duburs, Bull. Soc. Chim. Belg. 103 (1994) 299; (f) G. Galley, M. Pätzel, J. Chem. Soc., Perkin Trans. 1 1996, 2297; (g) A. W. M. Lee, W. H. Chan, Top. Curr. Chem. 190 (1997) 103; (h) S. Doye, T. Hotopp, E. Winterfeldt, Chem. Commun. 1997, 1491
    • J. Chem. Soc., Perkin Trans. 1 , vol.1996 , pp. 2297
    • Galley, G.1    Pätzel, M.2
  • 9
    • 0026730266 scopus 로고    scopus 로고
    • For more recent studies on sultones by other groups, see: (a) M. J. Perez-Perez, J. Balzarini, M. Hosova, E. De Clercq, M. J. Camarasa, Bioorg. Med. Chem. Lett. 2 (1992) 647; (b) W. B. Motherwell, A. M. K. Pennell, F. Ujjainwalla, J. Chem. Soc., Chem. Commun. 1992, 1067; (c) P. A. Crooks, R. C. Reynolds, J. A. Maddry, A. Rathore, M. S. Akhtar, J. A. Montgomery, J. A. I. Secrist, J. Org. Chem. 57 (1992) 2830; (d) N. Asao, M. Meguro, Y. Yamamoto, Synlett 1994, 185; (e) N. De Kimpe, M. Boeykens, L. Lazar, Z. Szakonyi, A. Kemme, G. Duburs, Bull. Soc. Chim. Belg. 103 (1994) 299; (f) G. Galley, M. Pätzel, J. Chem. Soc., Perkin Trans. 1 1996, 2297; (g) A. W. M. Lee, W. H. Chan, Top. Curr. Chem. 190 (1997) 103; (h) S. Doye, T. Hotopp, E. Winterfeldt, Chem. Commun. 1997, 1491
    • (1997) Top. Curr. Chem. , vol.190 , pp. 103
    • Lee, A.W.M.1    Chan, W.H.2
  • 10
    • 0026730266 scopus 로고    scopus 로고
    • For more recent studies on sultones by other groups, see: (a) M. J. Perez-Perez, J. Balzarini, M. Hosova, E. De Clercq, M. J. Camarasa, Bioorg. Med. Chem. Lett. 2 (1992) 647; (b) W. B. Motherwell, A. M. K. Pennell, F. Ujjainwalla, J. Chem. Soc., Chem. Commun. 1992, 1067; (c) P. A. Crooks, R. C. Reynolds, J. A. Maddry, A. Rathore, M. S. Akhtar, J. A. Montgomery, J. A. I. Secrist, J. Org. Chem. 57 (1992) 2830; (d) N. Asao, M. Meguro, Y. Yamamoto, Synlett 1994, 185; (e) N. De Kimpe, M. Boeykens, L. Lazar, Z. Szakonyi, A. Kemme, G. Duburs, Bull. Soc. Chim. Belg. 103 (1994) 299; (f) G. Galley, M. Pätzel, J. Chem. Soc., Perkin Trans. 1 1996, 2297; (g) A. W. M. Lee, W. H. Chan, Top. Curr. Chem. 190 (1997) 103; (h) S. Doye, T. Hotopp, E. Winterfeldt, Chem. Commun. 1997, 1491
    • (1491) Chem. Commun. , vol.1997
    • Doye, S.1    Hotopp, T.2    Winterfeldt, E.3
  • 11
    • 0000105081 scopus 로고
    • G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, eds., Thieme, Stuttgart
    • For reviews on intramolecular Diels-Alder reactions, see: (a) D. Craig, Houben-Weyl, Methods of Organic Chemistry, G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, eds., Vol. E 21 c, Thieme, Stuttgart 1995, p. 2872; (b) W. R. Roush, Comprehensive Organic Synthesis, B. M. Trost, I. Fleming, L. A. Paquette, eds., Pergamon Press, Oxford 1991, vol. 5, p. 513; (c) W. R. Roush, Advances in Cycloaddition, D. P. Curran, ed., vol. 2, Jai Press, Greenwich (CT) 1990, p. 91; (d) D. Craig, Chem. Soc. Rev. 16 (1987) 187; (e) D. F. Taber, Intramolecular Diels-Alder and Alder Ene Reactions, Springer, Berlin 1984; (f) A. G. Fallis, Can. J. Chem. 62 (1984) 183; (g) E. Ciganek, Org. React. 32 (1984) 1
    • (1995) Methods of Organic Chemistry , vol.E21C , pp. 2872
    • Craig, D.1    Houben-Weyl2
  • 12
    • 0003417469 scopus 로고
    • thesis, B. M. Trost, I. Fleming, L. A. Paquette, eds., Pergamon Press, Oxford
    • For reviews on intramolecular Diels-Alder reactions, see: (a) D. Craig, Houben-Weyl, Methods of Organic Chemistry, G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, eds., Vol. E 21 c, Thieme, Stuttgart 1995, p. 2872; (b) W. R. Roush, Comprehensive Organic Synthesis, B. M. Trost, I. Fleming, L. A. Paquette, eds., Pergamon Press, Oxford 1991, vol. 5, p. 513; (c) W. R. Roush, Advances in Cycloaddition, D. P. Curran, ed., vol. 2, Jai Press, Greenwich (CT) 1990, p. 91; (d) D. Craig, Chem. Soc. Rev. 16 (1987) 187; (e) D. F. Taber, Intramolecular Diels-Alder and Alder Ene Reactions, Springer, Berlin 1984; (f) A. G. Fallis, Can. J. Chem. 62 (1984) 183; (g) E. Ciganek, Org. React. 32 (1984) 1
    • (1991) Comprehensive Organic Syn , vol.5 , pp. 513
    • Roush, W.R.1
  • 13
    • 0002251962 scopus 로고
    • D. P. Curran, ed., Jai Press, Greenwich (CT)
    • For reviews on intramolecular Diels-Alder reactions, see: (a) D. Craig, Houben-Weyl, Methods of Organic Chemistry, G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, eds., Vol. E 21 c, Thieme, Stuttgart 1995, p. 2872; (b) W. R. Roush, Comprehensive Organic Synthesis, B. M. Trost, I. Fleming, L. A. Paquette, eds., Pergamon Press, Oxford 1991, vol. 5, p. 513; (c) W. R. Roush, Advances in Cycloaddition, D. P. Curran, ed., vol. 2, Jai Press, Greenwich (CT) 1990, p. 91; (d) D. Craig, Chem. Soc. Rev. 16 (1987) 187; (e) D. F. Taber, Intramolecular Diels-Alder and Alder Ene Reactions, Springer, Berlin 1984; (f) A. G. Fallis, Can. J. Chem. 62 (1984) 183; (g) E. Ciganek, Org. React. 32 (1984) 1
    • (1990) Advances in Cycloaddition , vol.2 , pp. 91
    • Roush, W.R.1
  • 14
    • 37049076286 scopus 로고
    • For reviews on intramolecular Diels-Alder reactions, see: (a) D. Craig, Houben-Weyl, Methods of Organic Chemistry, G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, eds., Vol. E 21 c, Thieme, Stuttgart 1995, p. 2872; (b) W. R. Roush, Comprehensive Organic Synthesis, B. M. Trost, I. Fleming, L. A. Paquette, eds., Pergamon Press, Oxford 1991, vol. 5, p. 513; (c) W. R. Roush, Advances in Cycloaddition, D. P. Curran, ed., vol. 2, Jai Press, Greenwich (CT) 1990, p. 91; (d) D. Craig, Chem. Soc. Rev. 16 (1987) 187; (e) D. F. Taber, Intramolecular Diels-Alder and Alder Ene Reactions, Springer, Berlin 1984; (f) A. G. Fallis, Can. J. Chem. 62 (1984) 183; (g) E. Ciganek, Org. React. 32 (1984) 1
    • (1987) Chem. Soc. Rev. , vol.16 , pp. 187
    • Craig, D.1
  • 15
    • 0003897657 scopus 로고
    • Springer, Berlin
    • For reviews on intramolecular Diels-Alder reactions, see: (a) D. Craig, Houben-Weyl, Methods of Organic Chemistry, G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, eds., Vol. E 21 c, Thieme, Stuttgart 1995, p. 2872; (b) W. R. Roush, Comprehensive Organic Synthesis, B. M. Trost, I. Fleming, L. A. Paquette, eds., Pergamon Press, Oxford 1991, vol. 5, p. 513; (c) W. R. Roush, Advances in Cycloaddition, D. P. Curran, ed., vol. 2, Jai Press, Greenwich (CT) 1990, p. 91; (d) D. Craig, Chem. Soc. Rev. 16 (1987) 187; (e) D. F. Taber, Intramolecular Diels-Alder and Alder Ene Reactions, Springer, Berlin 1984; (f) A. G. Fallis, Can. J. Chem. 62 (1984) 183; (g) E. Ciganek, Org. React. 32 (1984) 1
    • (1984) Intramolecular Diels-Alder and Alder Ene Reactions
    • Taber, D.F.1
  • 16
    • 0003360065 scopus 로고
    • For reviews on intramolecular Diels-Alder reactions, see: (a) D. Craig, Houben-Weyl, Methods of Organic Chemistry, G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, eds., Vol. E 21 c, Thieme, Stuttgart 1995, p. 2872; (b) W. R. Roush, Comprehensive Organic Synthesis, B. M. Trost, I. Fleming, L. A. Paquette, eds., Pergamon Press, Oxford 1991, vol. 5, p. 513; (c) W. R. Roush, Advances in Cycloaddition, D. P. Curran, ed., vol. 2, Jai Press, Greenwich (CT) 1990, p. 91; (d) D. Craig, Chem. Soc. Rev. 16 (1987) 187; (e) D. F. Taber, Intramolecular Diels-Alder and Alder Ene Reactions, Springer, Berlin 1984; (f) A. G. Fallis, Can. J. Chem. 62 (1984) 183; (g) E. Ciganek, Org. React. 32 (1984) 1
    • (1984) Can. J. Chem. , vol.62 , pp. 183
    • Fallis, A.G.1
  • 17
    • 0003009874 scopus 로고
    • For reviews on intramolecular Diels-Alder reactions, see: (a) D. Craig, Houben-Weyl, Methods of Organic Chemistry, G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, eds., Vol. E 21 c, Thieme, Stuttgart 1995, p. 2872; (b) W. R. Roush, Comprehensive Organic Synthesis, B. M. Trost, I. Fleming, L. A. Paquette, eds., Pergamon Press, Oxford 1991, vol. 5, p. 513; (c) W. R. Roush, Advances in Cycloaddition, D. P. Curran, ed., vol. 2, Jai Press, Greenwich (CT) 1990, p. 91; (d) D. Craig, Chem. Soc. Rev. 16 (1987) 187; (e) D. F. Taber, Intramolecular Diels-Alder and Alder Ene Reactions, Springer, Berlin 1984; (f) A. G. Fallis, Can. J. Chem. 62 (1984) 183; (g) E. Ciganek, Org. React. 32 (1984) 1
    • (1984) Org. React. , vol.32 , pp. 1
    • Ciganek, E.1
  • 18
    • 0003741398 scopus 로고
    • H. Distler, Angew. Chem. 77 (1965) 291; Angew. Chem. Int. Ed. Engl. 4 (1965) 300
    • (1965) Angew. Chem. , vol.77 , pp. 291
    • Distler, H.1
  • 19
    • 84981818041 scopus 로고
    • H. Distler, Angew. Chem. 77 (1965) 291; Angew. Chem. Int. Ed. Engl. 4 (1965) 300
    • (1965) Angew. Chem. Int. Ed. Engl. , vol.4 , pp. 300
  • 20
    • 0030772750 scopus 로고    scopus 로고
    • For a review on a related sequence involving intramolecular Diels-Alder reaction of silicon-tethered trienes and subsequent desilylation, see: L. Fensterbank, M. Malacria, S. McN. Sieburth, Synthesis 1997, 813
    • Synthesis , vol.1997 , pp. 813
    • Fensterbank, L.1    Malacria, M.2    Sieburth, S.McN.3
  • 34
    • 84990123074 scopus 로고
    • E. Bovenschulte, P. Metz, G. Henkel, Angew. Chem. 101 (1989) 204; Angew. Chem. Int. Ed. Engl. 28 (1989) 202
    • (1989) Angew. Chem. Int. Ed. Engl. , vol.28 , pp. 202
  • 37
    • 33748657657 scopus 로고
    • P. Metz, J. Stölting, M. Läge, B. Krebs, Angew. Chem. 106 (1994) 2275; Angew. Chem. Int. Ed. Engl. 33 (1994) 2195
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 2195
  • 41
    • 2742517238 scopus 로고    scopus 로고
    • unpublished
    • MeLi is superior to LDA for elimination of 12a to 23 (P. Metz, U. Meiners, unpublished)
    • Metz, P.1    Meiners, U.2
  • 42
    • 0003075009 scopus 로고    scopus 로고
    • For alternative direct additions of nucleophiles to 7-oxabicyclo[2.2.1]hept-5-ene derivatives followed by ring opening, see: (a) P. Chiu, M. Lautens, Top. Curr. Chem. 190 (1997) 1; (b) S. Woo, B. A. Keay, Synthesis 1996, 669
    • (1997) Top. Curr. Chem. , vol.190 , pp. 1
    • Chiu, P.1    Lautens, M.2
  • 43
    • 0029793274 scopus 로고    scopus 로고
    • For alternative direct additions of nucleophiles to 7-oxabicyclo[2.2.1]hept-5-ene derivatives followed by ring opening, see: (a) P. Chiu, M. Lautens, Top. Curr. Chem. 190 (1997) 1; (b) S. Woo, B. A. Keay, Synthesis 1996, 669
    • Synthesis , vol.1996 , pp. 669
    • Woo, S.1    Keay, B.A.2
  • 57
    • 33750173220 scopus 로고
    • (b) L. F. Tietze, U. Beifuss, Angew. Chem. 105 (1993) 137; Angew. Chem. Int. Ed. Engl. 32 (1993) 131;
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 131
  • 68
    • 2742586381 scopus 로고    scopus 로고
    • unpublished
    • MeLi is superior to LDA/TMEDA for elimination of 12e to 42 (P. Metz, J. Stölting, unpublished)
    • Metz, P.1    Stölting, J.2


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