메뉴 건너뛰기




Volumn 70, Issue 4, 2005, Pages 1497-1500

1,2-Acyl transfer reaction for the construction of multiple carbonyl-functionalized architecture by Sm(II)-induced tandem formation and breaking of cyclopropanol

Author keywords

[No Author keywords available]

Indexed keywords

KETONES; PROPANE; REDUCTION; SAMARIUM COMPOUNDS;

EID: 13844320898     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0402529     Document Type: Article
Times cited : (16)

References (43)
  • 2
    • 0042789931 scopus 로고
    • Radical 1,2-acyl rearrangement of 2-(haloalkyl)alkanones: (a) Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. (b) Kawafuchi, H.; Inokuchi, T. Tetrahedron Lett. 2002, 43, 2051-2054 and references cited therein.
    • (1993) Chem. Rev. , vol.93 , pp. 2091-2115
    • Dowd, P.1    Zhang, W.2
  • 3
    • 0037060983 scopus 로고    scopus 로고
    • and references cited therein
    • Radical 1,2-acyl rearrangement of 2-(haloalkyl)alkanones: (a) Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. (b) Kawafuchi, H.; Inokuchi, T. Tetrahedron Lett. 2002, 43, 2051-2054 and references cited therein.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 2051-2054
    • Kawafuchi, H.1    Inokuchi, T.2
  • 7
    • 0038682665 scopus 로고    scopus 로고
    • Recent application for [3 + 2] dipolar cycloaddition: (c) Yu, M.; Pagenkopf, B. L. J. Am. Chem. Soc. 2003, 125, 8122-8123. (d) Yu, M.; Pagenkopf, B. L. Org. Lett. 2003, 5, 5099-5101.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 8122-8123
    • Yu, M.1    Pagenkopf, B.L.2
  • 8
    • 0346025399 scopus 로고    scopus 로고
    • Recent application for [3 + 2] dipolar cycloaddition: (c) Yu, M.; Pagenkopf, B. L. J. Am. Chem. Soc. 2003, 125, 8122-8123. (d) Yu, M.; Pagenkopf, B. L. Org. Lett. 2003, 5, 5099-5101.
    • (2003) Org. Lett. , vol.5 , pp. 5099-5101
    • Yu, M.1    Pagenkopf, B.L.2
  • 9
    • 0001367782 scopus 로고
    • Wiley & Sons: New York
    • Reviews: (a) Molander, G. A. Organic Reactions; Wiley & Sons: New York, 1994; Vol. 46, pp 211-367. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354. (d) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15-23. (e) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961. (f) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745-777. (g) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, 422-438. (h) Tamiya, H.; Goto, K.; Matsuda, F. Org. Lett. 2004, 6, 545-547.
    • (1994) Organic Reactions , vol.46 , pp. 211-367
    • Molander, G.A.1
  • 10
    • 2142715741 scopus 로고    scopus 로고
    • Reviews: (a) Molander, G. A. Organic Reactions; Wiley & Sons: New York, 1994; Vol. 46, pp 211-367. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354. (d) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15-23. (e) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961. (f) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745-777. (g) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, 422-438. (h) Tamiya, H.; Goto, K.; Matsuda, F. Org. Lett. 2004, 6, 545-547.
    • (1996) Chem. Rev. , vol.96 , pp. 307-338
    • Molander, G.A.1    Harris, C.R.2
  • 11
    • 0032473838 scopus 로고    scopus 로고
    • Reviews: (a) Molander, G. A. Organic Reactions; Wiley & Sons: New York, 1994; Vol. 46, pp 211-367. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354. (d) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15-23. (e) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961. (f) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745-777. (g) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, 422-438. (h) Tamiya, H.; Goto, K.; Matsuda, F. Org. Lett. 2004, 6, 545-547.
    • (1998) Tetrahedron , vol.54 , pp. 3321-3354
    • Molander, G.A.1    Harris, C.R.2
  • 12
    • 0001948147 scopus 로고
    • Reviews: (a) Molander, G. A. Organic Reactions; Wiley & Sons: New York, 1994; Vol. 46, pp 211-367. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354. (d) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15-23. (e) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961. (f) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745-777. (g) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, 422-438. (h) Tamiya, H.; Goto, K.; Matsuda, F. Org. Lett. 2004, 6, 545-547.
    • (1991) Aldrichim. Acta , vol.24 , pp. 15-23
    • Soderquist, J.A.1
  • 13
    • 85022594998 scopus 로고
    • Reviews: (a) Molander, G. A. Organic Reactions; Wiley & Sons: New York, 1994; Vol. 46, pp 211-367. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354. (d) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15-23. (e) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961. (f) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745-777. (g) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, 422-438. (h) Tamiya, H.; Goto, K.; Matsuda, F. Org. Lett. 2004, 6, 545-547.
    • (1992) Synlett , pp. 943-961
    • Curran, D.P.1    Fevig, T.L.2    Jasperse, C.P.3    Totleben, M.J.4
  • 14
    • 0000209044 scopus 로고    scopus 로고
    • Reviews: (a) Molander, G. A. Organic Reactions; Wiley & Sons: New York, 1994; Vol. 46, pp 211-367. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354. (d) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15-23. (e) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961. (f) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745-777. (g) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, 422-438. (h) Tamiya, H.; Goto, K.; Matsuda, F. Org. Lett. 2004, 6, 545-547.
    • (1999) Chem. Rev. , vol.99 , pp. 745-777
    • Krief, A.1    Laval, A.-M.2
  • 15
    • 1442335547 scopus 로고    scopus 로고
    • Reviews: (a) Molander, G. A. Organic Reactions; Wiley & Sons: New York, 1994; Vol. 46, pp 211-367. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354. (d) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15-23. (e) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961. (f) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745-777. (g) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, 422-438. (h) Tamiya, H.; Goto, K.; Matsuda, F. Org. Lett. 2004, 6, 545-547.
    • (2004) Synlett , pp. 422-438
    • Berndt, M.1    Gross, S.2    Hölemann, A.3    Reissig, H.-U.4
  • 16
    • 1342311484 scopus 로고    scopus 로고
    • Reviews: (a) Molander, G. A. Organic Reactions; Wiley & Sons: New York, 1994; Vol. 46, pp 211-367. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354. (d) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15-23. (e) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961. (f) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745-777. (g) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, 422-438. (h) Tamiya, H.; Goto, K.; Matsuda, F. Org. Lett. 2004, 6, 545-547.
    • (2004) Org. Lett. , vol.6 , pp. 545-547
    • Tamiya, H.1    Goto, K.2    Matsuda, F.3
  • 17
    • 0348240161 scopus 로고
    • Cyclopropane formation with Sm(II) reagent: (a) Sasaki, M.; Collin, J.; Kagan, H. B. Tetrahedron Lett. 1988, 29, 6105-6106. (b) Fadel, A. Tetrahedron: Asymmetry 1994, 5, 531-534. (c) Iwaya, K.; Nakamura, M.; Hasegawa, E. Tetrahedron Lett. 2002, 43, 5067-5070. (d) Iwaya, K.; Tamura, M.; Nakamura, M.; Hasegawa, E. Tetrahedron Lett. 2003, 44, 9317-9320.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 6105-6106
    • Sasaki, M.1    Collin, J.2    Kagan, H.B.3
  • 18
    • 0028323229 scopus 로고
    • Cyclopropane formation with Sm(II) reagent: (a) Sasaki, M.; Collin, J.; Kagan, H. B. Tetrahedron Lett. 1988, 29, 6105-6106. (b) Fadel, A. Tetrahedron: Asymmetry 1994, 5, 531-534. (c) Iwaya, K.; Nakamura, M.; Hasegawa, E. Tetrahedron Lett. 2002, 43, 5067-5070. (d) Iwaya, K.; Tamura, M.; Nakamura, M.; Hasegawa, E. Tetrahedron Lett. 2003, 44, 9317-9320.
    • (1994) Tetrahedron: Asymmetry , vol.5 , pp. 531-534
    • Fadel, A.1
  • 19
    • 0037100021 scopus 로고    scopus 로고
    • Cyclopropane formation with Sm(II) reagent: (a) Sasaki, M.; Collin, J.; Kagan, H. B. Tetrahedron Lett. 1988, 29, 6105-6106. (b) Fadel, A. Tetrahedron: Asymmetry 1994, 5, 531-534. (c) Iwaya, K.; Nakamura, M.; Hasegawa, E. Tetrahedron Lett. 2002, 43, 5067-5070. (d) Iwaya, K.; Tamura, M.; Nakamura, M.; Hasegawa, E. Tetrahedron Lett. 2003, 44, 9317-9320.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 5067-5070
    • Iwaya, K.1    Nakamura, M.2    Hasegawa, E.3
  • 20
    • 0344441285 scopus 로고    scopus 로고
    • Cyclopropane formation with Sm(II) reagent: (a) Sasaki, M.; Collin, J.; Kagan, H. B. Tetrahedron Lett. 1988, 29, 6105-6106. (b) Fadel, A. Tetrahedron: Asymmetry 1994, 5, 531-534. (c) Iwaya, K.; Nakamura, M.; Hasegawa, E. Tetrahedron Lett. 2002, 43, 5067-5070. (d) Iwaya, K.; Tamura, M.; Nakamura, M.; Hasegawa, E. Tetrahedron Lett. 2003, 44, 9317-9320.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 9317-9320
    • Iwaya, K.1    Tamura, M.2    Nakamura, M.3    Hasegawa, E.4
  • 30
    • 13844310573 scopus 로고    scopus 로고
    • note
    • 12a and alkylideneacetoacetates as a dienophile. See the Supporting Information for experimental details.
  • 37
    • 13844312165 scopus 로고    scopus 로고
    • note
    • 2. (Chemical Equation Presented)
  • 43
    • 0001283395 scopus 로고
    • Review about the synthesis of bridgehead olefins: Warner, P. M. Chem. Rev. 1989, 89, 1067-1093.
    • (1989) Chem. Rev. , vol.89 , pp. 1067-1093
    • Warner, P.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.