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Volumn 128, Issue 20, 2006, Pages 6745-6754

Sequential Ru-Pd catalysis: A two-catalyst one-pot protocol for the synthesis of N- and O-heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYSIS; METALS; NITROGEN; PALLADIUM; SYNTHESIS (CHEMICAL); THERMODYNAMICS;

EID: 33646749523     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja060812g     Document Type: Article
Times cited : (93)

References (104)
  • 27
    • 0037288242 scopus 로고    scopus 로고
    • Ru is known to catalyze allylic ionization and allylic substitution reactions: (a) Renaud, J.-L.; Bruneau, C.; Demerseman, B. Synlett 2003, 3, 408.
    • (2003) Synlett , vol.3 , pp. 408
    • Renaud, J.-L.1    Bruneau, C.2    Demerseman, B.3
  • 38
    • 33646740615 scopus 로고    scopus 로고
    • note
    • 3 catalyst.
  • 62
    • 33646737016 scopus 로고    scopus 로고
    • note
    • Enantioselective cyclization using boron cocatalysis has been achieved, see ref 15.
  • 64
    • 0035859355 scopus 로고    scopus 로고
    • Enantioselective allylic cyclizations of alkoxy nucleophiles were developed independently and concurrently with this work: (b) Jiang, L.; Burke, S. D. Org. Lett. 2001, 3, 1953.
    • (2001) Org. Lett. , vol.3 , pp. 1953
    • Jiang, L.1    Burke, S.D.2
  • 66
    • 33646743593 scopus 로고    scopus 로고
    • note
    • Matched implies that the catalyst reinforces the natural diastereoselectivity of the substrate, and mismatched implies that the catalyst contradicts the natural diastereoselectivity.
  • 67
    • 33646749334 scopus 로고    scopus 로고
    • note
    • 1H NMR techniques. In particular, the presence of a strong NOE (generally between 5% and 10%) for cis 2,6- and 2,5-disubstituted compounds was observed between protons adjacent to the heteroatom. The corresponding absence of this NOE confirmed the trans stereochemical assignment of the opposite diastereomer. Furthermore, since the absolute stereochemistry of the starting substrate is known, the absolute configuration of the newly created allylic stereogenic center is also known.
  • 69
    • 33646719300 scopus 로고    scopus 로고
    • note
    • See compound 85 in the Supporting Information.
  • 72
    • 33646731571 scopus 로고    scopus 로고
    • note
    • For definitions of matched and mismatched with respect to the working model see ref 11.
  • 73
    • 0003553884 scopus 로고
    • McGreer, E. G., Olney, J. W., McGreer, D. L., Eds.; Raven Press: New York, and references therein
    • Kainic Acid as a Tool in Neurobiology; McGreer, E. G., Olney, J. W., McGreer, D. L., Eds.; Raven Press: New York, 1978 and references therein.
    • (1978) Kainic Acid As a Tool in Neurobiology
  • 75
    • 33646746423 scopus 로고    scopus 로고
    • note
    • We are very grateful to Douglas W. Young for sending a copy of his original spectra.
  • 85
    • 0003397781 scopus 로고    scopus 로고
    • Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinhein, Germany
    • Metal Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinhein, Germany, 1998.
    • (1998) Metal Catalyzed Cross-Coupling Reactions
  • 101
    • 33646741013 scopus 로고    scopus 로고
    • note
    • Higher overall yields were obtained when the hydroboration was performed before carbonylation.
  • 102
    • 0035932595 scopus 로고    scopus 로고
    • Other routes have accomplished syntheses of similar pieces with the exocyclic olefin stereochemistry installed in 14 steps: (a) Vakalopoulos, A.; Lampe, T. F. J.; Hoffmann, H. M. R. Org. Lett. 2001, 3, 929.
    • (2001) Org. Lett. , vol.3 , pp. 929
    • Vakalopoulos, A.1    Lampe, T.F.J.2    Hoffmann, H.M.R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.