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Volumn 9, Issue 24, 2007, Pages 5063-5066

Organocatalyzed cyclizations of π-allylpalladium complexes: A new method for the construction of five- and six-membered rings

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ORGANOMETALLIC COMPOUND; PALLADIUM; PYRROLIDINE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 36849014339     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7023554     Document Type: Article
Times cited : (110)

References (26)
  • 3
    • 0037569997 scopus 로고    scopus 로고
    • For comprehensive reviews, see: a, Negishi, E.-i, Ed, de Meijere, A, Assoc. Ed, J. Wiley & Sons: New York, Chapter V, p
    • For comprehensive reviews, see: (a) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed., de Meijere, A., Assoc. Ed.; J. Wiley & Sons: New York, 2002; Vol. 2, Chapter V, p 1669.
    • (2002) Handbook of Organopalladium Chemistry for Organic Synthesis , vol.2 , pp. 1669
  • 4
    • 84942767100 scopus 로고
    • Wilkinson, G, Stone, F. G. A, Abel, E. W, Eds, Pergamon: Oxford
    • (b) Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 8, p 799.
    • (1982) Comprehensive Organometallic Chemistry , vol.8 , pp. 799
    • Trost, B.M.1    Verhoeven, T.R.2
  • 5
    • 0042379988 scopus 로고    scopus 로고
    • For review articles on catalytic asymmetric allylation with π-allyl palladium complexes, see: a
    • For review articles on catalytic asymmetric allylation with π-allyl palladium complexes, see: (a) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921.
    • (2003) Chem. Rev , vol.103 , pp. 2921
    • Trost, B.M.1    Crawley, M.L.2
  • 6
    • 0003445429 scopus 로고    scopus 로고
    • Jacobsen, E. N, Pfaltz, A, Yamamoto, H, Eds, Springer-Verlag: Heidelberg
    • (b) Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, 2000; p 833.
    • (2000) Comprehensive Asymmetric Catalysis , pp. 833
    • Pfaltz, A.1    Lautens, M.2
  • 9
    • 33750610453 scopus 로고    scopus 로고
    • Int. Ed, and references therein
    • Braun, M.; Meier, T. Angew. Chem., Int. Ed. 2006, 45, 6952 and references therein.
    • (2006) Angew. Chem , vol.45 , pp. 6952
    • Braun, M.1    Meier, T.2
  • 11
    • 36849022455 scopus 로고    scopus 로고
    • House, H., O. Modern Synthetic Reactions, 2nd ed.; The Benjamin/ Cummins Publishing Company: Menlo Park, 1972; p 494.
    • House, H., O. Modern Synthetic Reactions, 2nd ed.; The Benjamin/ Cummins Publishing Company: Menlo Park, 1972; p 494.
  • 17
    • 36849016234 scopus 로고    scopus 로고
    • A review article on eliminations of π-allyl palladium derivatives: I. Shimizu, in ref 2a, p 1981.
    • A review article on eliminations of π-allyl palladium derivatives: I. Shimizu, in ref 2a), p 1981.
  • 23
    • 36849043474 scopus 로고    scopus 로고
    • The 8th issue of Acc. Chem. Res. 2004, 37, several reviews on organocatalysis.
    • (d) The 8th issue of Acc. Chem. Res. 2004, 37, several reviews on organocatalysis.
  • 25
    • 36849057492 scopus 로고    scopus 로고
    • Preparation of 16: Pyrrolidine (123.6 mg, 145 μL, 1.74 mmol) was added to a solution of tetrakis(triphenylphosphine)palladium (183 mg, 0.174 mmol) and aldehyde 11 (542 mg, 1.15 mmol) in THF (250 mL, with stirring, under an argon atmosphere. After 1.5 h the solvent was removed under reduced pressure, and the concentrate was taken up in dichloromethane (150 mL, The solution was washed with 2% aq HCl, water, aq NaHCO3, and brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. Purification by dry-flash chromatography (SiO2, eluent 3% ethyl acetate in petroleum ether) afforded 458 mg (96, of the title compound 16, as a colorless oil. Physical data for 16: IRfilm: 2933, 2862, 1725, 1255, 1073, 1040, 837, 777, 700. 1H NMR (δ, 9.50 (d, J, 3.0 Hz, 1H, 7.27-7.36 (m, 5H, 5.86-6.04 (m, 1H, 5.05-5.14 (m, 2H, 4.54 (s, 2H, 3.67 (dd, J 1, 2.2 Hz, J2, 3.7 Hz, 1H, 3.41 dd, J1
    • 3Si: C 71.08, H 9.34; found: C 71.08, H 9.49.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.