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Volumn , Issue 1, 1996, Pages 105-110

Tricarbonyls: Reactive model dienophiles for asymmetric Diels-Alder reactions

Author keywords

2 methyl 1 (1 phenylalkoxy) 1,3 butadienes; allox ane; dimethyldioxirane; hetero Diels Alder reaction; indanetrione

Indexed keywords

KETONE;

EID: 0030071588     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4154     Document Type: Article
Times cited : (8)

References (54)
  • 1
    • 0000048258 scopus 로고
    • Intermolecular Diels-Alder Reactions
    • Trost, B. M., Ed.; Pergamon, Oxford
    • Oppolzer, W.: Intermolecular Diels-Alder Reactions, in Comprehensive Organic Synthesis; Trost, B. M., Ed.; Vol. 5, Pergamon, Oxford, 1991, p 315-399. Carruthers, W.: Cycloaddition Reactions in Organic Synthesis; Pergamon, Oxford, 1990.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 315-399
    • Oppolzer, W.1
  • 2
    • 0003523008 scopus 로고
    • Pergamon, Oxford
    • Oppolzer, W.: Intermolecular Diels-Alder Reactions, in Comprehensive Organic Synthesis; Trost, B. M., Ed.; Vol. 5, Pergamon, Oxford, 1991, p 315-399. Carruthers, W.: Cycloaddition Reactions in Organic Synthesis; Pergamon, Oxford, 1990.
    • (1990) Cycloaddition Reactions in Organic Synthesis
    • Carruthers, W.1
  • 3
    • 0000556633 scopus 로고
    • For some recent references on chiral dienophiles, see: (a) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602 (b) Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153. (c) Oppolzer, W.; Seletsky, B. M.; Bernardinelli, G. Tetrahedron Lett. 1994, 35, 3509. (d) Saito, T.; Karakasa, T.; Fujii, H.; Furuno, E.; Suda, H.; Kobayashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1359.
    • (1994) J. Org. Chem. , vol.59 , pp. 4602
    • Ritter, A.R.1    Miller, M.J.2
  • 4
    • 12044252424 scopus 로고
    • For some recent references on chiral dienophiles, see: (a) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602 (b) Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153. (c) Oppolzer, W.; Seletsky, B. M.; Bernardinelli, G. Tetrahedron Lett. 1994, 35, 3509. (d) Saito, T.; Karakasa, T.; Fujii, H.; Furuno, E.; Suda, H.; Kobayashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1359.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 6153
    • Maruoka, K.1    Akakura, M.2    Saito, S.3    Ooi, T.4    Yamamoto, H.5
  • 5
    • 0028291727 scopus 로고
    • For some recent references on chiral dienophiles, see: (a) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602 (b) Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153. (c) Oppolzer, W.; Seletsky, B. M.; Bernardinelli, G. Tetrahedron Lett. 1994, 35, 3509. (d) Saito, T.; Karakasa, T.; Fujii, H.; Furuno, E.; Suda, H.; Kobayashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1359.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 3509
    • Oppolzer, W.1    Seletsky, B.M.2    Bernardinelli, G.3
  • 6
    • 37049072123 scopus 로고
    • For some recent references on chiral dienophiles, see: (a) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602 (b) Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153. (c) Oppolzer, W.; Seletsky, B. M.; Bernardinelli, G. Tetrahedron Lett. 1994, 35, 3509. (d) Saito, T.; Karakasa, T.; Fujii, H.; Furuno, E.; Suda, H.; Kobayashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1359.
    • (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 1359
    • Saito, T.1    Karakasa, T.2    Fujii, H.3    Furuno, E.4    Suda, H.5    Kobayashi, K.6
  • 7
    • 0027963432 scopus 로고
    • For some recent references on asymmetric Diels-Alder catalysts, see: (a) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623. (b) Kobayashi, S.; Araki, M.; Hachiya, J. J. Org. Chem. 1994, 59, 3758. (c) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (d) Motoyama, Y.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 1563. (e) Corey, E. J.; Guzman-Perez, A.; Loh, T.-P. J. Am. Chem. Soc. 1994, 116, 3611. (f) Engler, T. A.; Letavic, M. A.; Lynch, K. O.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179. (g) Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561. (h) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935.
    • (1994) Tetrahedron , vol.50 , pp. 11623
    • Kobayashi, S.1    Ishitani, H.2    Hachiya, I.3    Araki, M.4
  • 8
    • 0000082453 scopus 로고
    • For some recent references on asymmetric Diels-Alder catalysts, see: (a) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623. (b) Kobayashi, S.; Araki, M.; Hachiya, J. J. Org. Chem. 1994, 59, 3758. (c) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (d) Motoyama, Y.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 1563. (e) Corey, E. J.; Guzman-Perez, A.; Loh, T.-P. J. Am. Chem. Soc. 1994, 116, 3611. (f) Engler, T. A.; Letavic, M. A.; Lynch, K. O.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179. (g) Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561. (h) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935.
    • (1994) J. Org. Chem. , vol.59 , pp. 3758
    • Kobayashi, S.1    Araki, M.2    Hachiya, J.3
  • 9
    • 0000210159 scopus 로고
    • For some recent references on asymmetric Diels-Alder catalysts, see: (a) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623. (b) Kobayashi, S.; Araki, M.; Hachiya, J. J. Org. Chem. 1994, 59, 3758. (c) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (d) Motoyama, Y.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 1563. (e) Corey, E. J.; Guzman-Perez, A.; Loh, T.-P. J. Am. Chem. Soc. 1994, 116, 3611. (f) Engler, T. A.; Letavic, M. A.; Lynch, K. O.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179. (g) Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561. (h) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 2812
    • Mikami, K.1    Motoyama, Y.2    Terada, M.3
  • 10
    • 0006386674 scopus 로고
    • For some recent references on asymmetric Diels-Alder catalysts, see: (a) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623. (b) Kobayashi, S.; Araki, M.; Hachiya, J. J. Org. Chem. 1994, 59, 3758. (c) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (d) Motoyama, Y.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 1563. (e) Corey, E. J.; Guzman-Perez, A.; Loh, T.-P. J. Am. Chem. Soc. 1994, 116, 3611. (f) Engler, T. A.; Letavic, M. A.; Lynch, K. O.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179. (g) Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561. (h) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935.
    • (1994) J. Chem. Soc., Chem. Commun. , pp. 1563
    • Motoyama, Y.1    Mikami, K.2
  • 11
    • 0028232984 scopus 로고
    • For some recent references on asymmetric Diels-Alder catalysts, see: (a) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623. (b) Kobayashi, S.; Araki, M.; Hachiya, J. J. Org. Chem. 1994, 59, 3758. (c) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (d) Motoyama, Y.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 1563. (e) Corey, E. J.; Guzman-Perez, A.; Loh, T.-P. J. Am. Chem. Soc. 1994, 116, 3611. (f) Engler, T. A.; Letavic, M. A.; Lynch, K. O.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179. (g) Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561. (h) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 3611
    • Corey, E.J.1    Guzman-Perez, A.2    Loh, T.-P.3
  • 12
    • 1842267370 scopus 로고
    • For some recent references on asymmetric Diels-Alder catalysts, see: (a) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623. (b) Kobayashi, S.; Araki, M.; Hachiya, J. J. Org. Chem. 1994, 59, 3758. (c) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (d) Motoyama, Y.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 1563. (e) Corey, E. J.; Guzman-Perez, A.; Loh, T.-P. J. Am. Chem. Soc. 1994, 116, 3611. (f) Engler, T. A.; Letavic, M. A.; Lynch, K. O.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179. (g) Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561. (h) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935.
    • (1994) J. Org. Chem. , vol.59 , pp. 1179
    • Engler, T.A.1    Letavic, M.A.2    Lynch, K.O.3    Takusagawa, F.4
  • 13
    • 0000778261 scopus 로고
    • For some recent references on asymmetric Diels-Alder catalysts, see: (a) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623. (b) Kobayashi, S.; Araki, M.; Hachiya, J. J. Org. Chem. 1994, 59, 3758. (c) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (d) Motoyama, Y.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 1563. (e) Corey, E. J.; Guzman-Perez, A.; Loh, T.-P. J. Am. Chem. Soc. 1994, 116, 3611. (f) Engler, T. A.; Letavic, M. A.; Lynch, K. O.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179. (g) Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561. (h) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 1561
    • Ishihara, K.1    Yamamoto, H.2
  • 14
    • 0026059649 scopus 로고
    • For some recent references on asymmetric Diels-Alder catalysts, see: (a) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623. (b) Kobayashi, S.; Araki, M.; Hachiya, J. J. Org. Chem. 1994, 59, 3758. (c) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (d) Motoyama, Y.; Mikami, K. J. Chem. Soc., Chem. Commun. 1994, 1563. (e) Corey, E. J.; Guzman-Perez, A.; Loh, T.-P. J. Am. Chem. Soc. 1994, 116, 3611. (f) Engler, T. A.; Letavic, M. A.; Lynch, K. O.; Takusagawa, F. J. Org. Chem. 1994, 59, 1179. (g) Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561. (h) Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 935
    • Terada, M.1    Mikami, K.2    Nakai, T.3
  • 15
    • 0001076469 scopus 로고
    • For some recent references on chiral dienes, see: (a) Bloch, R.; Chaptal-Gradoz, N. J. Org. Chem. 1994, 59, 4162. (b) Tietze, L. F.; Schneider, C.; Montenbruck, A. Angew. Chem. 1994, 106, 1031. (c) Arce, E.; Carreno, M. C.; Cid, M. B.; Ruano, J. L. G. J. Org. Chem. 1994, 59, 3421. (d) Enders, D.; Meyer, O.; Raabe, G.; Runsink, J. Synthesis 1994, 66. (e) Barluenga, J.; Aznar, F.; Valdes, C.; Martin, A.; Garcia-Granda, S.; Martin, E. J. Am. Chem. Soc. 1993, 115, 4403. (f) Enders, D.; Meyer, O.; Raabe, G. Synthesis 1992, 1242.
    • (1994) J. Org. Chem. , vol.59 , pp. 4162
    • Bloch, R.1    Chaptal-Gradoz, N.2
  • 16
    • 0344278429 scopus 로고
    • For some recent references on chiral dienes, see: (a) Bloch, R.; Chaptal-Gradoz, N. J. Org. Chem. 1994, 59, 4162. (b) Tietze, L. F.; Schneider, C.; Montenbruck, A. Angew. Chem. 1994, 106, 1031. (c) Arce, E.; Carreno, M. C.; Cid, M. B.; Ruano, J. L. G. J. Org. Chem. 1994, 59, 3421. (d) Enders, D.; Meyer, O.; Raabe, G.; Runsink, J. Synthesis 1994, 66. (e) Barluenga, J.; Aznar, F.; Valdes, C.; Martin, A.; Garcia-Granda, S.; Martin, E. J. Am. Chem. Soc. 1993, 115, 4403. (f) Enders, D.; Meyer, O.; Raabe, G. Synthesis 1992, 1242.
    • (1994) Angew. Chem. , vol.106 , pp. 1031
    • Tietze, L.F.1    Schneider, C.2    Montenbruck, A.3
  • 17
    • 0001692899 scopus 로고
    • For some recent references on chiral dienes, see: (a) Bloch, R.; Chaptal-Gradoz, N. J. Org. Chem. 1994, 59, 4162. (b) Tietze, L. F.; Schneider, C.; Montenbruck, A. Angew. Chem. 1994, 106, 1031. (c) Arce, E.; Carreno, M. C.; Cid, M. B.; Ruano, J. L. G. J. Org. Chem. 1994, 59, 3421. (d) Enders, D.; Meyer, O.; Raabe, G.; Runsink, J. Synthesis 1994, 66. (e) Barluenga, J.; Aznar, F.; Valdes, C.; Martin, A.; Garcia-Granda, S.; Martin, E. J. Am. Chem. Soc. 1993, 115, 4403. (f) Enders, D.; Meyer, O.; Raabe, G. Synthesis 1992, 1242.
    • (1994) J. Org. Chem. , vol.59 , pp. 3421
    • Arce, E.1    Carreno, M.C.2    Cid, M.B.3    Ruano, J.L.G.4
  • 18
    • 0028203787 scopus 로고
    • For some recent references on chiral dienes, see: (a) Bloch, R.; Chaptal-Gradoz, N. J. Org. Chem. 1994, 59, 4162. (b) Tietze, L. F.; Schneider, C.; Montenbruck, A. Angew. Chem. 1994, 106, 1031. (c) Arce, E.; Carreno, M. C.; Cid, M. B.; Ruano, J. L. G. J. Org. Chem. 1994, 59, 3421. (d) Enders, D.; Meyer, O.; Raabe, G.; Runsink, J. Synthesis 1994, 66. (e) Barluenga, J.; Aznar, F.; Valdes, C.; Martin, A.; Garcia-Granda, S.; Martin, E. J. Am. Chem. Soc. 1993, 115, 4403. (f) Enders, D.; Meyer, O.; Raabe, G. Synthesis 1992, 1242.
    • (1994) Synthesis , pp. 66
    • Enders, D.1    Meyer, O.2    Raabe, G.3    Runsink, J.4
  • 19
    • 0000651283 scopus 로고
    • For some recent references on chiral dienes, see: (a) Bloch, R.; Chaptal-Gradoz, N. J. Org. Chem. 1994, 59, 4162. (b) Tietze, L. F.; Schneider, C.; Montenbruck, A. Angew. Chem. 1994, 106, 1031. (c) Arce, E.; Carreno, M. C.; Cid, M. B.; Ruano, J. L. G. J. Org. Chem. 1994, 59, 3421. (d) Enders, D.; Meyer, O.; Raabe, G.; Runsink, J. Synthesis 1994, 66. (e) Barluenga, J.; Aznar, F.; Valdes, C.; Martin, A.; Garcia-Granda, S.; Martin, E. J. Am. Chem. Soc. 1993, 115, 4403. (f) Enders, D.; Meyer, O.; Raabe, G. Synthesis 1992, 1242.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 4403
    • Barluenga, J.1    Aznar, F.2    Valdes, C.3    Martin, A.4    Garcia-Granda, S.5    Martin, E.6
  • 20
    • 0026736881 scopus 로고
    • For some recent references on chiral dienes, see: (a) Bloch, R.; Chaptal-Gradoz, N. J. Org. Chem. 1994, 59, 4162. (b) Tietze, L. F.; Schneider, C.; Montenbruck, A. Angew. Chem. 1994, 106, 1031. (c) Arce, E.; Carreno, M. C.; Cid, M. B.; Ruano, J. L. G. J. Org. Chem. 1994, 59, 3421. (d) Enders, D.; Meyer, O.; Raabe, G.; Runsink, J. Synthesis 1994, 66. (e) Barluenga, J.; Aznar, F.; Valdes, C.; Martin, A.; Garcia-Granda, S.; Martin, E. J. Am. Chem. Soc. 1993, 115, 4403. (f) Enders, D.; Meyer, O.; Raabe, G. Synthesis 1992, 1242.
    • (1992) Synthesis , pp. 1242
    • Enders, D.1    Meyer, O.2    Raabe, G.3
  • 21
    • 0001640244 scopus 로고
    • Reactions of Activated Dienes with Aldehydes
    • Trost, B. M., Ed.; Pergamon, Oxford
    • Bednarski, M. D.; Lyssikatos, J. P.: Reactions of Activated Dienes with Aldehydes, in Comprehensive Organic Synthesis; Trost, B. M., Ed.; Vol. 2, Pergamon, Oxford, 1991, p 661-706. Weinreb, S. M.: Heterodienophile Additions to Dienes, in Comprehensive Organic Synthesis; Trost, B. M., Ed.; Vol. 5, Pergamon, Oxford, 1991, p 401-449.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 661-706
    • Bednarski, M.D.1    Lyssikatos, J.P.2
  • 22
    • 0000730407 scopus 로고
    • Heterodienophile Additions to Dienes
    • Trost, B. M., Ed.; Pergamon, Oxford
    • Bednarski, M. D.; Lyssikatos, J. P.: Reactions of Activated Dienes with Aldehydes, in Comprehensive Organic Synthesis; Trost, B. M., Ed.; Vol. 2, Pergamon, Oxford, 1991, p 661-706. Weinreb, S. M.: Heterodienophile Additions to Dienes, in Comprehensive Organic Synthesis; Trost, B. M., Ed.; Vol. 5, Pergamon, Oxford, 1991, p 401-449.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 401-449
    • Weinreb, S.M.1
  • 23
    • 0028264476 scopus 로고
    • and lit. cit. therein
    • Waldmann, H. Synthesis 1994, 535 and lit. cit. therein.
    • (1994) Synthesis , pp. 535
    • Waldmann, H.1
  • 32
    • 0001767875 scopus 로고
    • (a) Hunter, C. A. Angew. Chem. 1993, 105, 1653; Angew. Chem., Int. Ed. Engl. 1993, 32, 1584 and lit. cit. therein.
    • (1993) Angew. Chem. , vol.105 , pp. 1653
    • Hunter, C.A.1
  • 33
    • 33748228968 scopus 로고
    • and lit. cit. therein
    • (a) Hunter, C. A. Angew. Chem. 1993, 105, 1653; Angew. Chem., Int. Ed. Engl. 1993, 32, 1584 and lit. cit. therein.
    • (1993) Angew. Chem., Int. Ed. Engl. , vol.32 , pp. 1584
  • 54
    • 9044254560 scopus 로고    scopus 로고
    • note
    • Further details of the crystal structure analyses are available on request from the Fachinformationszentrum Karlsruhe GmbH, D-76344 Eggenstein-Leopoldshafen (Germany), on quoting the deposition number CSD-59157, the names of the authors, and journal citation.


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