메뉴 건너뛰기




Volumn 72, Issue 13, 2007, Pages 4877-4881

Palladium-catalyzed cyclization of 1,ω-dienols: Multiple ways to intramolecularly trap a carbocation

Author keywords

[No Author keywords available]

Indexed keywords

CARBOCATIONS; DIENOLS; PINACOL REARRANGEMENT; REOXIDATION;

EID: 34250832086     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0705871     Document Type: Article
Times cited : (23)

References (51)
  • 3
    • 34047094938 scopus 로고    scopus 로고
    • For several recent forum articles on this topic see: a
    • For several recent forum articles on this topic see: (a) Cornell, C. N.; Sigman, M. S. Inorg. Chem. 2007, 46, 1903-1909.
    • (2007) Inorg. Chem , vol.46 , pp. 1903-1909
    • Cornell, C.N.1    Sigman, M.S.2
  • 9
    • 0345511748 scopus 로고    scopus 로고
    • For early cases with stoichiometric quantities of Pd(II), see: (a) Trebellas, J. C.; Olechovski, J. R.; Jonassen, H. B. J. Organomet. Chem. 1966, 6, 412-420.
    • For early cases with stoichiometric quantities of Pd(II), see: (a) Trebellas, J. C.; Olechovski, J. R.; Jonassen, H. B. J. Organomet. Chem. 1966, 6, 412-420.
  • 12
    • 37049133967 scopus 로고    scopus 로고
    • Brown, E. D.; Sam, T. W.; Sutherland, J.; K.; Torre, A. J. Chem. Soc., Perkin Trans. 1 1975, 2326-2332.
    • (d) Brown, E. D.; Sam, T. W.; Sutherland, J.; K.; Torre, A. J. Chem. Soc., Perkin Trans. 1 1975, 2326-2332.
  • 14
    • 4544321004 scopus 로고
    • Electron withdrawing groups can cause nonfragmenting pathways to dominate, see
    • Electron withdrawing groups can cause nonfragmenting pathways to dominate, see: Overman, L. E.; Renaldo, A. F. Tetrahedron Lett. 1983, 24, 2235-2238.
    • (1983) Tetrahedron Lett , vol.24 , pp. 2235-2238
    • Overman, L.E.1    Renaldo, A.F.2
  • 15
    • 2442620654 scopus 로고    scopus 로고
    • For several examples where a nucleophilic alkene (enol, indole, etc, leads to a cyclic product, see: a
    • For several examples where a nucleophilic alkene (enol, indole, etc.) leads to a cyclic product, see: (a) Widenhoefer, R. A. Pure Appl. Chem. 2004, 76, 671-678.
    • (2004) Pure Appl. Chem , vol.76 , pp. 671-678
    • Widenhoefer, R.A.1
  • 21
    • 34249004522 scopus 로고    scopus 로고
    • Despite how the reaction is shown to proceed in Scheme 2, we suspect that a free carbocation is not likely to form and that the phenol serves to stabilize developing charge. This notion is supported by DFT studies with pincer ligated Pt-dicationic catalysts. See: Nowroozi-Isfahani, T.; Musaev, D. G.; Morokuma, K.; Gagné, M. R. Organometallics 2007, 26, 2540-2549.
    • Despite how the reaction is shown to proceed in Scheme 2, we suspect that a free carbocation is not likely to form and that the phenol serves to stabilize developing charge. This notion is supported by DFT studies with pincer ligated Pt-dicationic catalysts. See: Nowroozi-Isfahani, T.; Musaev, D. G.; Morokuma, K.; Gagné, M. R. Organometallics 2007, 26, 2540-2549.
  • 29
    • 0037036759 scopus 로고    scopus 로고
    • We and others have also sought methods that activate alkenes toward nucleophilic attack, but otherwise inhibit β-H elimination as a default method of catalytic turnover. (a) Hahn, C.; Cucciolito, M. E.; Vitagliano, A. J. Am. Chem. Soc. 2002, 124, 9038-9039.
    • We and others have also sought methods that activate alkenes toward nucleophilic attack, but otherwise inhibit β-H elimination as a default method of catalytic turnover. (a) Hahn, C.; Cucciolito, M. E.; Vitagliano, A. J. Am. Chem. Soc. 2002, 124, 9038-9039.
  • 49
    • 20444497757 scopus 로고    scopus 로고
    • For a recent review of oxy-palladation of alkenes, see
    • For a recent review of oxy-palladation of alkenes, see: Muzart, J. Tetrahedron 2005, 61, 5955-6008.
    • (2005) Tetrahedron , vol.61 , pp. 5955-6008
    • Muzart, J.1
  • 50
    • 33748724931 scopus 로고    scopus 로고
    • Hydrogenation of unsaturated ketones 22 and 23 proceeds with carbonyl reduction, see: (a) Sajiki, H.; Hattori, K.; Hirota, K. J. Chem. Soc., Perkin Trans. 1 1998, 4043-4044.
    • Hydrogenation of unsaturated ketones 22 and 23 proceeds with carbonyl reduction, see: (a) Sajiki, H.; Hattori, K.; Hirota, K. J. Chem. Soc., Perkin Trans. 1 1998, 4043-4044.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.