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Volumn 11, Issue 17, 2000, Pages 3585-3590

Enantioselective formation of quaternary centers on β-ketoesters with chiral palladium QUIPHOS catalyst

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; PALLADIUM;

EID: 0034622891     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00337-2     Document Type: Article
Times cited : (44)

References (11)
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    • (a) Pfaltz, A.; Lautens, M. Allylic Substitution Reactions. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. II, Chapter 24, pp. 831-884. (b) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1994; pp. 325-365. (c) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-365. (c) Williams, J. M. J. Synlett 1996, 705-710. (d) Porte, A. M.; Reibenspies, J.; Burgess, K. J. Am. Chem. Soc. 1998, 120, 9180-9187. (e) Oslob, J.; Akermark, B.; Helquist, P.; Norrby, P. O. Orgonometallics 1997, 16, 3015-3021. (f) Pena-Cabrera, E.; Norrby, P. O.; Sjogren, M.; Vitagliano, A.; De Felice, V.; Oslob, J.; Ishii, S.; O'Neill, D.; Akermark, B.; Helkist, P. J. Am. Chem. Soc. 1996, 118, 4299-4313.
  • 2
    • 0007769160 scopus 로고    scopus 로고
    • (a) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-401. (b) Fuji, K. Chem. Rev. 1993, 93, 2037-2066. (c) Martin, S. F. Tetrahedron 1980, 36, 419-460.
  • 3
    • 0007810985 scopus 로고    scopus 로고
    • (a) Trost, B. M.; Radinov, R.; Grenzer, E. M. J. Am. Chem. Soc. 1997, 119, 7879-7880. (b) Trost, B. M.; Ariza, X. J. Am. Chem. Soc. 1999, 121, 10727-10737. (c) Kuwano, R.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 3236-3237. (d) Trost, B. M.; Schroeder, G. M. J. Org. Chem. 2000, 65, 1569-1573.
  • 4
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    • (a) Von Matt, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566. (b) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769. (c) Frost, C. G.; Williams, J. M. J. Tetrahedron Lett. 1993, 34, 2015.
  • 6
    • 0007858412 scopus 로고    scopus 로고
    • Several studies provide strong evidence that the nucleophile preferentially attacks the longer Pd-C bond trans to the P atom: Computational studies: (a) Blochl, P. E.; Togni, A. Organometallics 1996, 15, 4125-4132. (b) Ward, T. R. Organometallics 1996, 15, 2836. NMR investigations: (c) Steinhagen, H.; Reggelin, M.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2108. (d) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031.
  • 7
    • 0007763010 scopus 로고    scopus 로고
    • (a) Brunel, J. M.; Constantieux, T.; Labande, A.; Lubatti, F.; Buono, G. Tetrahedron Lett. 1997, 38, 5971-5974. (b) Constantieux, T.; Brunel, J. M.; Labande, A.; Buono, G. Synlett 1998, 49-50. (c) Muchow, G.; Brunel, J. M.; Maffei, M.; Pardigon, O.; Buono, G. Tetrahedron 1998, 54, 10435-10448. (d) Brunel, J. M.; Constantieux, T.; Buono, G. J. Org. Chem. 1999, 64, 8940-8942.
  • 8
    • 0007864694 scopus 로고    scopus 로고
    • It is noteworthy that QUIPHOS 2 has been also successfully used as ligand in an enantioselective copper catalyzed Diels-Alder reaction and an asymmetric conjugate addition of diethylzinc to enones. (a) Brunel, J. M.; Del Campo, B.; Buono, G. Tetrahedron Lett. 1998, 39, 9663-9666. (b) Delapierre, G.; Constantieux, T.; Brunel, J. M.; Buono, G. Eur. J. Org. Chem. 2000, 2507-2511.
  • 9
    • 0007762244 scopus 로고    scopus 로고
    • The absolute configuration of major enantiomer of 3 was determined by correlation with the known product (see Ref. 3).
  • 10
    • 0007866113 scopus 로고    scopus 로고
    • 3) 26.4, 27.6, 27.8, 29.0, 29.7, 54.6, 66.1, 66.9, 124.4, 126.6, 126.9, 128.0, 128.6, 129.7, 133.9, 136.6, 139.4, 143.6, 172.4, 194.5.
  • 11
    • 0007763011 scopus 로고    scopus 로고
    • Interestingly, the diastereomer 16b observed in our conditions has been notified as the minor diastereomer formed under Trost conditions (see Ref. 3).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.