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Volumn , Issue 10, 1999, Pages 1563-1566

Asymmetric allylic alkylation using a palladium complex of chiral 2- (phosphinoaryl)pyridine ligands

Author keywords

Asymmetric allylic alkylations; Asymmetric catalysis; Chiral P,N ligands; Palladium

Indexed keywords

PALLADIUM COMPLEX;

EID: 0032843585     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2916     Document Type: Article
Times cited : (57)

References (43)
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    • Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds; Pergamon Press: Oxford
    • b) Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds; Pergamon Press: Oxford, 1982, Vol. 8, pp. 799.
    • (1982) Comprehensive Organometallic Chemistry , vol.8 , pp. 799
    • Trost, B.M.1    Verhoeven, T.R.2
  • 6
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    • b) Trost, B. M.; Krueger, A. C.; Bunt, R. C.; Zambrano, J. J. Am. Chem. Soc. 1996, 118, 6520. The best enantioselectivity (92% ee) in the so far reported allylic alkylations of 1,3-dimethyl-substituted allyl substrates reaction has been achieved by using cyclohexanediamidodiphosphine-Pd complex as a catalyst. However, the catalyst can not be successfully applied to 1,3-diphenyl-substituted allyl substrate.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 6520
    • Trost, B.M.1    Krueger, A.C.2    Bunt, R.C.3    Zambrano, J.4
  • 8
    • 33748227479 scopus 로고
    • Some recent examples of asymmetric allylic substitution of 1,3-disubstituted allyl substrates using P,N-chelate ligands: a) von Matt, P.; Pfaltz, A. Angew. Chem. Int. Ed. Engl. 1993, 32, 566.
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 566
    • Von Matt, P.1    Pfaltz, A.2
  • 28
    • 0032536559 scopus 로고    scopus 로고
    • Efficient regio-and enantioselective allylic alkylation of 1-and 3-aryl-2-propenyl acetates has been reported with chiral palladium catalysts: a) Pretoto, R.; Pfaltz, A. Angew. Chem. Int. Ed. Engl. 1998, 37, 323.
    • (1998) Angew. Chem. Int. Ed. Engl. , vol.37 , pp. 323
    • Pretoto, R.1    Pfaltz, A.2
  • 30
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    • For regio-and enantioselective allylic alkylation using the catalysts other than palladium catalysts, see: c) Lloyd-Jones, G. C.; Pfaltz, A. Angew. Chem. Int. Ed. Engl. 1995, 34, 462.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 462
    • Lloyd-Jones, G.C.1    Pfaltz, A.2
  • 33
    • 0032538768 scopus 로고    scopus 로고
    • Highly enantioselective allylic alkylation of cyclic allyl substrates using P,N-chelate ligands has also been reported: Kudis, S.; Helmchen, G. Angew. Chem. Int. Ed. Engl. 1998, 37, 3047.
    • (1998) Angew. Chem. Int. Ed. Engl. , vol.37 , pp. 3047
    • Kudis, S.1    Helmchen, G.2
  • 41
    • 0344245455 scopus 로고    scopus 로고
    • note
    • In contrary to our results, Helmchen et al reported that high enantioselectivity was observed using sodium hydride as the base in THF with their new phosphinooxazoline-palladium complex (reference 5p).
  • 42
    • 0344245454 scopus 로고    scopus 로고
    • note
    • The formation of the corresponding (Z) product was not detected spectroscopically.
  • 43
    • 0344676956 scopus 로고    scopus 로고
    • note
    • 3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.