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Volumn 5, Issue 5, 2003, Pages 657-660

Aldol- and Mannich-type reactions via in situ olefin migration in ionic liquid

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALLYL ALCOHOL; IMINE; RUBIDIUM CHLORIDE; BICYCLO COMPOUND; BIOMIMETIC MATERIAL; PYRONE DERIVATIVE;

EID: 0038543276     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0273102     Document Type: Article
Times cited : (104)

References (42)
  • 4
    • 0000324975 scopus 로고
    • (a) Sato, S.; Matsuda, I.; Shibata, M. J. Organomet. Chem. 1989, 377, 347. (b) Matsuda, I.; Shibata, M.; Sato, S. J. Organomet. Chem. 1988, 340, C5. For use of Rh-enolate intermediates in aldol reactions, see: (c) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938. (d) Sato, S. ; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517.
    • (1989) J. Organomet. Chem. , vol.377 , pp. 347
    • Sato, S.1    Matsuda, I.2    Shibata, M.3
  • 5
    • 0001890665 scopus 로고
    • (a) Sato, S.; Matsuda, I.; Shibata, M. J. Organomet. Chem. 1989, 377, 347. (b) Matsuda, I.; Shibata, M.; Sato, S. J. Organomet. Chem. 1988, 340, C5. For use of Rh-enolate intermediates in aldol reactions, see: (c) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938. (d) Sato, S. ; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517.
    • (1988) J. Organomet. Chem. , vol.340
    • Matsuda, I.1    Shibata, M.2    Sato, S.3
  • 6
    • 0000556498 scopus 로고
    • (a) Sato, S.; Matsuda, I.; Shibata, M. J. Organomet. Chem. 1989, 377, 347. (b) Matsuda, I.; Shibata, M.; Sato, S. J. Organomet. Chem. 1988, 340, C5. For use of Rh-enolate intermediates in aldol reactions, see: (c) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938. (d) Sato, S. ; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 938
    • Slough, G.A.1    Bergman, R.G.2    Heathcock, C.H.3
  • 7
    • 0000756559 scopus 로고
    • (a) Sato, S.; Matsuda, I.; Shibata, M. J. Organomet. Chem. 1989, 377, 347. (b) Matsuda, I.; Shibata, M.; Sato, S. J. Organomet. Chem. 1988, 340, C5. For use of Rh-enolate intermediates in aldol reactions, see: (c) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938. (d) Sato, S. ; Matsuda, I.; Izumi, Y. Tetrahedron Lett. 1986, 27, 5517.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 5517
    • Sato, S.1    Matsuda, I.2    Izumi, Y.3
  • 8
    • 0035833675 scopus 로고    scopus 로고
    • For examples, see: (a) Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. (b) Murahashi, S.; Takaya, H. Acc. Chem. Res. 2000, 33, 225. (c) Lin, Y. R.; Zhou, X. T.; Dai, L. X.; Sun, J. J. Org. Chem. 1997, 62, 1799. (d) Picquet, M.; Bruneau, C.; Dixneuf, P. M. Tetrahedron 1999, 55, 3937. (f) Gómez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553.
    • (2001) Org. Lett. , vol.3 , pp. 2497
    • Trost, B.M.1    Silcoff, E.R.2    Ito, H.3
  • 9
    • 0034008092 scopus 로고    scopus 로고
    • For examples, see: (a) Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. (b) Murahashi, S.; Takaya, H. Acc. Chem. Res. 2000, 33, 225. (c) Lin, Y. R.; Zhou, X. T.; Dai, L. X.; Sun, J. J. Org. Chem. 1997, 62, 1799. (d) Picquet, M.; Bruneau, C.; Dixneuf, P. M. Tetrahedron 1999, 55, 3937. (f) Gómez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 225
    • Murahashi, S.1    Takaya, H.2
  • 10
    • 0001353802 scopus 로고    scopus 로고
    • For examples, see: (a) Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. (b) Murahashi, S.; Takaya, H. Acc. Chem. Res. 2000, 33, 225. (c) Lin, Y. R.; Zhou, X. T.; Dai, L. X.; Sun, J. J. Org. Chem. 1997, 62, 1799. (d) Picquet, M.; Bruneau, C.; Dixneuf, P. M. Tetrahedron 1999, 55, 3937. (f) Gómez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553.
    • (1997) J. Org. Chem. , vol.62 , pp. 1799
    • Lin, Y.R.1    Zhou, X.T.2    Dai, L.X.3    Sun, J.4
  • 11
    • 0033605839 scopus 로고    scopus 로고
    • For examples, see: (a) Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. (b) Murahashi, S.; Takaya, H. Acc. Chem. Res. 2000, 33, 225. (c) Lin, Y. R.; Zhou, X. T.; Dai, L. X.; Sun, J. J. Org. Chem. 1997, 62, 1799. (d) Picquet, M.; Bruneau, C.; Dixneuf, P. M. Tetrahedron 1999, 55, 3937. (f) Gómez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553.
    • (1999) Tetrahedron , vol.55 , pp. 3937
    • Picquet, M.1    Bruneau, C.2    Dixneuf, P.M.3
  • 12
    • 0029796652 scopus 로고    scopus 로고
    • For examples, see: (a) Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497. (b) Murahashi, S.; Takaya, H. Acc. Chem. Res. 2000, 33, 225. (c) Lin, Y. R.; Zhou, X. T.; Dai, L. X.; Sun, J. J. Org. Chem. 1997, 62, 1799. (d) Picquet, M.; Bruneau, C.; Dixneuf, P. M. Tetrahedron 1999, 55, 3937. (f) Gómez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 8553
    • Gómez-Bengoa, E.1    Cuerva, J.M.2    Mateo, C.3    Echavarren, A.M.4
  • 15
    • 0035938397 scopus 로고    scopus 로고
    • 3 as a catalyst to carry out the aldol reaction. No reaction was observed without the lithium co-reagent. See: Uma, R.; Davis, M.; Crévisy, C.; Grée, R. Tetrahedron Lett. 2001, 42, 3069.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 3069
    • Uma, R.1    Davis, M.2    Crévisy, C.3    Grée, R.4
  • 18
    • 0004252595 scopus 로고    scopus 로고
    • Blackie Academic and Professional: Glasgow
    • (c). Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic and Professional: Glasgow, 1998.
    • (1998) Organic Synthesis in Water
    • Grieco, P.A.1
  • 29
    • 0000712108 scopus 로고
    • For other examples of Ru enolates, see: (a) Hartwig, J. F.; Bergman, R. G.; Anderson, R. A. Organometallics 1991, 10, 3326. (b) Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852. (c) Chang, S.; Na, Y.; Choi, E.; Kim, S. Org. Lett. 2001, 3, 2089. (d) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067.
    • (1991) Organometallics , vol.10 , pp. 3326
    • Hartwig, J.F.1    Bergman, R.G.2    Anderson, R.A.3
  • 30
    • 0001200566 scopus 로고    scopus 로고
    • For other examples of Ru enolates, see: (a) Hartwig, J. F.; Bergman, R. G.; Anderson, R. A. Organometallics 1991, 10, 3326. (b) Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852. (c) Chang, S.; Na, Y.; Choi, E.; Kim, S. Org. Lett. 2001, 3, 2089. (d) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067.
    • (1996) Organometallics , vol.15 , pp. 2852
    • Rasley, B.T.1    Rapta, M.2    Kulawiec, R.J.3
  • 31
    • 0000793297 scopus 로고    scopus 로고
    • For other examples of Ru enolates, see: (a) Hartwig, J. F.; Bergman, R. G.; Anderson, R. A. Organometallics 1991, 10, 3326. (b) Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852. (c) Chang, S.; Na, Y.; Choi, E.; Kim, S. Org. Lett. 2001, 3, 2089. (d) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067.
    • (2001) Org. Lett. , vol.3 , pp. 2089
    • Chang, S.1    Na, Y.2    Choi, E.3    Kim, S.4
  • 32
    • 0035385137 scopus 로고    scopus 로고
    • For other examples of Ru enolates, see: (a) Hartwig, J. F.; Bergman, R. G.; Anderson, R. A. Organometallics 1991, 10, 3326. (b) Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852. (c) Chang, S.; Na, Y.; Choi, E.; Kim, S. Org. Lett. 2001, 3, 2089. (d) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067.
    • (2001) Chem. Rev. , vol.101 , pp. 2067
    • Trost, B.M.1    Toste, F.D.2    Pinkerton, A.B.3
  • 33
    • 0034706016 scopus 로고    scopus 로고
    • Previously, Ru-enol intermediates have been captured by aldehydes in a Michael addition reaction: (a) Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 2000, 122, 8081. For capturing of Pd and Pt enolates by aldehydes, see: (b) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (c) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032. (d) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 8081
    • Trost, B.M.1    Pinkerton, A.B.2
  • 34
    • 0032542749 scopus 로고    scopus 로고
    • Previously, Ru-enol intermediates have been captured by aldehydes in a Michael addition reaction: (a) Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 2000, 122, 8081. For capturing of Pd and Pt enolates by aldehydes, see: (b) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (c) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032. (d) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 2474
    • Hagiwara, E.1    Fujii, A.2    Sodeoka, M.3
  • 35
    • 0032494425 scopus 로고    scopus 로고
    • Previously, Ru-enol intermediates have been captured by aldehydes in a Michael addition reaction: (a) Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 2000, 122, 8081. For capturing of Pd and Pt enolates by aldehydes, see: (b) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (c) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032. (d) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 10032
    • Fujimura, O.1
  • 36
    • 0000263137 scopus 로고
    • Previously, Ru-enol intermediates have been captured by aldehydes in a Michael addition reaction: (a) Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 2000, 122, 8081. For capturing of Pd and Pt enolates by aldehydes, see: (b) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474. (c) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032. (d) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648.
    • (1995) J. Org. Chem. , vol.60 , pp. 2648
    • Sodeoka, M.1    Ohrai, K.2    Shibasaki, M.3
  • 42
    • 0141551329 scopus 로고    scopus 로고
    • note
    • 4. The mixture was then concentrated under reduced pressure. The residue was purified by preparatory TLC on silica gel to afford the desired aldol product.


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