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Volumn 121, Issue 28, 1999, Pages 6759-6760

Palladium-catalyzed asymmetric alkylation of ketone enolates [7]

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; PALLADIUM;

EID: 0033591944     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991135b     Document Type: Letter
Times cited : (258)

References (31)
  • 1
    • 0032473509 scopus 로고    scopus 로고
    • Corey, E. J. Angew. Chem., Int. Ed. Engl. 1998, 388. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994. Fuji, K. Chem. Rev. 1993, 93, 2037.
    • (1998) Angew. Chem., Int. Ed. Engl. , pp. 388
    • Corey, E.J.1
  • 3
    • 0001521888 scopus 로고
    • Corey, E. J. Angew. Chem., Int. Ed. Engl. 1998, 388. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994. Fuji, K. Chem. Rev. 1993, 93, 2037.
    • (1993) Chem. Rev. , vol.93 , pp. 2037
    • Fuji, K.1
  • 6
    • 0030664209 scopus 로고    scopus 로고
    • Ahman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918. Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 11108
    • Palucki, M.1    Buchwald, S.L.2
  • 7
    • 84985534954 scopus 로고
    • Bhattacharya, A.; Dolling, U-H.; Grabowski, E. J. J.; Karady, S.; Ryan, K. M.; Weinstock, L. M. Angew, Chem., Int. Ed. Engl. 1986, 25, 476. Conn, R. S. E.; Lowell, A. V.; Karady, S.; Weinstock, L. M. J. Org. Chem. 1986, 51, 4710. Dolling, U.-H.; Davis, P.; Grabowski, E. J. J. J. Am. Chem. Soc. 1984, 104, 446. Hughes, D. L.; Dolling, U.-H.; Ryan, K. M.; Schoenewaldt, E. F.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 4745.
    • (1986) Angew, Chem., Int. Ed. Engl. , vol.25 , pp. 476
    • Bhattacharya, A.1    Dolling, U.-H.2    Grabowski, E.J.J.3    Karady, S.4    Ryan, K.M.5    Weinstock, L.M.6
  • 8
    • 0000867232 scopus 로고
    • Bhattacharya, A.; Dolling, U-H.; Grabowski, E. J. J.; Karady, S.; Ryan, K. M.; Weinstock, L. M. Angew, Chem., Int. Ed. Engl. 1986, 25, 476. Conn, R. S. E.; Lowell, A. V.; Karady, S.; Weinstock, L. M. J. Org. Chem. 1986, 51, 4710. Dolling, U.-H.; Davis, P.; Grabowski, E. J. J. J. Am. Chem. Soc. 1984, 104, 446. Hughes, D. L.; Dolling, U.-H.; Ryan, K. M.; Schoenewaldt, E. F.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 4745.
    • (1986) J. Org. Chem. , vol.51 , pp. 4710
    • Conn, R.S.E.1    Lowell, A.V.2    Karady, S.3    Weinstock, L.M.4
  • 9
    • 33845470711 scopus 로고
    • Bhattacharya, A.; Dolling, U-H.; Grabowski, E. J. J.; Karady, S.; Ryan, K. M.; Weinstock, L. M. Angew, Chem., Int. Ed. Engl. 1986, 25, 476. Conn, R. S. E.; Lowell, A. V.; Karady, S.; Weinstock, L. M. J. Org. Chem. 1986, 51, 4710. Dolling, U.-H.; Davis, P.; Grabowski, E. J. J. J. Am. Chem. Soc. 1984, 104, 446. Hughes, D. L.; Dolling, U.-H.; Ryan, K. M.; Schoenewaldt, E. F.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 4745.
    • (1984) J. Am. Chem. Soc. , vol.104 , pp. 446
    • Dolling, U.-H.1    Davis, P.2    Grabowski, E.J.J.3
  • 10
    • 0000637655 scopus 로고
    • Bhattacharya, A.; Dolling, U-H.; Grabowski, E. J. J.; Karady, S.; Ryan, K. M.; Weinstock, L. M. Angew, Chem., Int. Ed. Engl. 1986, 25, 476. Conn, R. S. E.; Lowell, A. V.; Karady, S.; Weinstock, L. M. J. Org. Chem. 1986, 51, 4710. Dolling, U.-H.; Davis, P.; Grabowski, E. J. J. J. Am. Chem. Soc. 1984, 104, 446. Hughes, D. L.; Dolling, U.-H.; Ryan, K. M.; Schoenewaldt, E. F.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 4745.
    • (1987) J. Org. Chem. , vol.52 , pp. 4745
    • Hughes, D.L.1    Dolling, U.-H.2    Ryan, K.M.3    Schoenewaldt, E.F.4    Grabowski, E.J.J.5
  • 13
    • 6844254916 scopus 로고    scopus 로고
    • For reviews of the palladium-catalyzed allylic alkylation reaction, see: Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I, Ed.; VCH Publishers: New York, 1993. Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857. Fiaud, J. C. In Metal-Promoted Selectivity in Organic Synthesis; Graziani, M., Hubert, A. J., Noels, A. F., Eds.; Kluwer Academic Publishers: Dordrecht, 1991. Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
    • (1996) Chem. Rev. , vol.96 , pp. 395
    • Trost, B.M.1    Van Vranken, D.L.2
  • 14
    • 0028890597 scopus 로고
    • For reviews of the palladium-catalyzed allylic alkylation reaction, see: Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I, Ed.; VCH Publishers: New York, 1993. Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857. Fiaud, J. C. In Metal-Promoted Selectivity in Organic Synthesis; Graziani, M., Hubert, A. J., Noels, A. F., Eds.; Kluwer Academic Publishers: Dordrecht, 1991. Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
    • (1995) Tetrahedron , vol.51 , pp. 975
    • Heumann, A.1    Reglier, M.2
  • 15
    • 6844254916 scopus 로고    scopus 로고
    • Ojima, I, Ed.; VCH Publishers: New York
    • For reviews of the palladium-catalyzed allylic alkylation reaction, see: Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I, Ed.; VCH Publishers: New York, 1993. Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857. Fiaud, J. C. In Metal-Promoted Selectivity in Organic Synthesis; Graziani, M., Hubert, A. J., Noels, A. F., Eds.; Kluwer Academic Publishers: Dordrecht, 1991. Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
    • (1993) Catalytic Asymmetric Synthesis
    • Hayashi, T.1
  • 16
    • 0042250061 scopus 로고
    • For reviews of the palladium-catalyzed allylic alkylation reaction, see: Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I, Ed.; VCH Publishers: New York, 1993. Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857. Fiaud, J. C. In Metal-Promoted Selectivity in Organic Synthesis; Graziani, M., Hubert, A. J., Noels, A. F., Eds.; Kluwer Academic Publishers: Dordrecht, 1991. Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
    • (1992) Chem. Rev. , vol.92 , pp. 857
    • Sawamura, M.1    Ito, Y.2
  • 17
    • 6844254916 scopus 로고    scopus 로고
    • Graziani, M., Hubert, A. J., Noels, A. F., Eds.; Kluwer Academic Publishers: Dordrecht
    • For reviews of the palladium-catalyzed allylic alkylation reaction, see: Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I, Ed.; VCH Publishers: New York, 1993. Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857. Fiaud, J. C. In Metal-Promoted Selectivity in Organic Synthesis; Graziani, M., Hubert, A. J., Noels, A. F., Eds.; Kluwer Academic Publishers: Dordrecht, 1991. Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
    • (1991) Metal-Promoted Selectivity in Organic Synthesis
    • Fiaud, J.C.1
  • 18
    • 0024302311 scopus 로고
    • For reviews of the palladium-catalyzed allylic alkylation reaction, see: Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I, Ed.; VCH Publishers: New York, 1993. Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857. Fiaud, J. C. In Metal-Promoted Selectivity in Organic Synthesis; Graziani, M., Hubert, A. J., Noels, A. F., Eds.; Kluwer Academic Publishers: Dordrecht, 1991. Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
    • (1989) Chem. Rev. , vol.89 , pp. 257
    • Consiglio, G.1    Waymouth, R.M.2
  • 19
    • 0000782153 scopus 로고
    • Trost, B. M.; Self, C. R. J. Org. Chem. 1984, 49, 468. Trost, B. M.; Keinan, E. Tetrahedron Lett. 1980, 21, 2591.
    • (1984) J. Org. Chem. , vol.49 , pp. 468
    • Trost, B.M.1    Self, C.R.2
  • 22
    • 0345116776 scopus 로고    scopus 로고
    • note
    • This assignment required hydroboration-oxidation of the alkene and ketone reduction to produce diastereomeric diols whose relative and absolute stereochemistry were established by NMR methods. Details appear in the Supporting Information.
  • 27
    • 0345548070 scopus 로고    scopus 로고
    • note
    • Two equivalents of allyl acetate were used in the experiment performed at - 10 °C.
  • 29
    • 0006488342 scopus 로고
    • Dieter, R. K.; Lin, Y. J.; Dieter, J. W. J. Org. Chem. 1984, 49, 3183. Trost, B. M.; Stanton, J. L. J. Am. Chem. Soc. 1975, 97, 4018.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 4018
    • Trost, B.M.1    Stanton, J.L.2
  • 31
    • 0033515721 scopus 로고    scopus 로고
    • After submission of this manuscript, the report of the alkylation of the lithium enolate of 2-substituted tetralones generated from enol silyl ethers using chiral amine inducers appeared, see: Yamashita, Y.; Odashima, K.; Koga, K. Tetrahedron Lett. 1999, 40, 2803.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2803
    • Yamashita, Y.1    Odashima, K.2    Koga, K.3


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