메뉴 건너뛰기




Volumn 124, Issue 38, 2002, Pages 11246-11247

Allenes as carbon nucleophiles in palladium-catalyzed reactions: Observation of anti attack of allenes on (π-allyl)palladium complexes

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; PALLADIUM COMPLEX;

EID: 0037174418     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja026150m     Document Type: Article
Times cited : (48)

References (52)
  • 4
    • 0003417469 scopus 로고
    • Trost, B. M., Flemming, I., Semmelhack, M. F., Eds; Pergamon: Oxford, Chapter 3.3
    • Godleski, S. A. In Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Semmelhack, M. F., Eds; Pergamon: Oxford, 1991; Vol. 4, Chapter. 3.3.
    • (1991) Comprehensive Organic Synthesis , vol.4
    • Godleski, S.A.1
  • 21
    • 0003445429 scopus 로고    scopus 로고
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds; Springer-Verlag: Berlin, Heidelberg, New York. Chapter 24
    • Pfaltz, A.; Lautens, M. In Comprehensive Asymmetric Catalysis I-III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds; Springer-Verlag: Berlin, Heidelberg, New York. 1999; Chapter 24.
    • (1999) Comprehensive Asymmetric Catalysis I-III
    • Pfaltz, A.1    Lautens, M.2
  • 22
    • 0010501711 scopus 로고    scopus 로고
    • note
    • 12c,d as likely pathways.
  • 29
    • 0031004898 scopus 로고    scopus 로고
    • (d) Allylsilanes were shown to attack a Pd(diene) complex leading to a trans-carbopalladation of the double bond: Castaño, A. M.; Persson, B. A.; Bäckvall, J. E. Chem. Eur. J. 1997, 3, 482.
    • (1997) Chem. Eur. J. , vol.3 , pp. 482
    • Castaño, A.M.1    Persson, B.A.2    Bäckvall, J.E.3
  • 38
    • 0010421158 scopus 로고    scopus 로고
    • note
    • 0) or inversion (heat) afforded the starting material 1 (see Supporting Information).
  • 39
    • 0010500305 scopus 로고    scopus 로고
    • note
    • 1H NMR (NOE, coupling constants).
  • 40
    • 0010460843 scopus 로고    scopus 로고
    • note
    • The trifluoroacetate esters 4 was prepared via ester hydrolysis of the corresponding pivalate esters cis-1, yielding the corresponding alcohols which were treated with trifluoroacetic anhydride.
  • 42
    • 0010500306 scopus 로고    scopus 로고
    • note
    • 2 at room temperature a mixture of starting material (4), 2a, and A was observed. After 30 min at room-temperature all 4 was consumed, and the major compound obtained was A together with 2a. Compound A is presumably formed via trapping of the tertiary carbocation by Pd(0). Heating A to 70-80°C for 2 h gave 3.
  • 45
    • 0010460844 scopus 로고    scopus 로고
    • See ref 13d
    • (b) See ref 13d
  • 48
    • 0010420299 scopus 로고    scopus 로고
    • note
    • cis-5 and trans-5 are readily available from 1,3-cycloheptadiene via the chloroacyloxylation approach (cf. refs 4 and 5a).
  • 52
    • 0010421294 scopus 로고    scopus 로고
    • note
    • One reviewer suggested that Pd(0) is assisting in the nucleophilic attack by coordinating to the allene. This is a possible pathway that we cannot exclude.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.