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Volumn 65, Issue 5, 2000, Pages 1569-1573

Palladium-catalyzed asymmetric allylic alkylation of barbituric acid derivatives: Enantioselective syntheses of cyclopentobarbital and pentobarbital

Author keywords

[No Author keywords available]

Indexed keywords

BARBITURIC ACID DERIVATIVE; CYCLOPENTOBARBITAL; PENTOBARBITAL; UNCLASSIFIED DRUG;

EID: 0034629278     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991491c     Document Type: Article
Times cited : (48)

References (15)
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    • For recent reviews, 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 Inc.; 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.
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    • Brunner, H.; Ruckert, T. Monatsh. Chem. 1998,129, 339. Brunner, H.; Fürst, J. Inorg. Chim. Acta 1994, 220, 63.
    • Brunner, H.; Demi, I.; Dirnberger, W.; Nuber, B.; Reisser, \V. EUT. J. Inorg. Chem. 1998, 43. Brunner, H.; Ruckert, T. Monatsh. Chem. 1998,129, 339. Brunner, H.; Fürst, J. Inorg. Chim. Acta 1994, 220, 63.
    • (1998) EUT. J. Inorg. Chem. , vol.43
    • Brunner, H.1    Demi, I.2    Dirnberger, W.3    Nuber, B.4    Reisser, V.5
  • 4
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    • Trost, B. M.; Radinov, R.; Grenzer, E. M. J. Am. Chem. Soc. 1997,119, 7879. Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1988, 53, 113.
    • For examples of chiral induction at the nucleophile in the AAA reaction, see: Trost, B. M.; Schroeder, G. M. J. Am. Chem. Soc. 1999, 121, 6759. Trost, B. M.; Radinov, R.; Grenzer, E. M. J. Am. Chem. Soc. 1997,119, 7879. Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1988, 53, 113.
    • (1999) Am. Chem. Soc. , vol.121 , pp. 6759
    • Trost, B.M.1    Schroeder, G.M.2
  • 7
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    • See Trost and Van Vranken in ref 2.
    • See Trost and Van Vranken in ref 2.
  • 9
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    • Knabe, J.; Philipson, K. Arch. Pharm. (Weinheim) 1966, 299, 232. Meidereri E. C.; Shonle, H. A. J. Am. Chem. Sac. 1934, 56, 1772.
    • Carroll, F. L; Meek, R. J. Org. Chem. 1969,34, 2676. Knabe, J.; Philipson, K. Arch. Pharm. (Weinheim) 1966, 299, 232. Meidereri E. C.; Shonle, H. A. J. Am. Chem. Sac. 1934, 56, 1772.
    • (1969) J. Org. Chem. , vol.34 , pp. 2676
    • Carroll, F.L.1    Meek, R.2
  • 12
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    • The absolute configuration was determined by comparison of the rotation to that reported in the literature (ref 9). Thus, using the (R.R)-Ll, (fl)-9 was obtained.
    • The absolute configuration was determined by comparison of the rotation to that reported in the literature (ref 9). Thus, using the (R.R)-Ll, (fl)-9 was obtained.
  • 13
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    • Gibson, W. R.; Doran, W. J.; Wood, W. C.; Swanson, E. C. J. Pharmocol. Exp. Ther. 1959, 125, 23. Kricglstein, J.; Mwasekaga, S. Arzeim. Forsch. 1987, 37, 291.
    • Doran, W. J. J. Org. Chem. 1960, 25, 1737. Gibson, W. R.; Doran, W. J.; Wood, W. C.; Swanson, E. C. J. Pharmocol. Exp. Ther. 1959, 125, 23. Kricglstein, J.; Mwasekaga, S. Arzeim. Forsch. 1987, 37, 291.
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    • E. Lilly & Co. US 2872448, 1956. Doran, W. J. Chem. Abstr. 1959, 53, 13185.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.