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Volumn 48, Issue 44, 2007, Pages 7801-7804

Protected propargylic acetals. Nicholas-Prins cyclization leading to functionalized 2-alkynyl-tetrahydropyrans. Intramolecular trapping by allenes

Author keywords

Alkyne complexes; Carbocations; Nicholas reaction; Prins cyclization; Tetrahydropyrans

Indexed keywords

ACETAL DERIVATIVE; ALLENE DERIVATIVE; ALLYL ALCOHOL; COBALT COMPLEX; HOMOALLENIC ALCOHOL; HOMOALLYLIC ALCOHOL; LEWIS ACID; PROPARGYLIC ACETAL DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34848899797     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.021     Document Type: Article
Times cited : (19)

References (34)
  • 1
    • 0346265937 scopus 로고
    • Abel E.W., Stone F.G., Wilkinson G., and Hegedus L.S. (Eds), Pergamon, Oxford Chapter 7.1
    • Caffyn A.J., and Nicholas K.M. In: Abel E.W., Stone F.G., Wilkinson G., and Hegedus L.S. (Eds). Comprehensive Organometallic Chemistry II Vol. 12 (1995), Pergamon, Oxford Chapter 7.1
    • (1995) Comprehensive Organometallic Chemistry II , vol.12
    • Caffyn, A.J.1    Nicholas, K.M.2
  • 13
    • 33646403425 scopus 로고    scopus 로고
    • Tetrahydropyran units are encountered in many natural products, for selected examples, see:
    • Tetrahydropyran units are encountered in many natural products, for selected examples, see:. Clarke P.A., and Santos S. Eur. J. Org. Chem. (2006) 2045
    • (2006) Eur. J. Org. Chem. , pp. 2045
    • Clarke, P.A.1    Santos, S.2
  • 16
    • 33747432576 scopus 로고    scopus 로고
    • For strategies involving Prins reaction see also:
    • For strategies involving Prins reaction see also:. Vasconcellos M.L.A.A., and Miranda L.S.M. Quim. Nova 29 (2006) 834
    • (2006) Quim. Nova , vol.29 , pp. 834
    • Vasconcellos, M.L.A.A.1    Miranda, L.S.M.2
  • 19
    • 0025935199 scopus 로고
    • For the formation of 2-aryl-tetrahydropyrans from arene-chromiumtricarbonyl complexes, through a similar pathway see:
    • For the formation of 2-aryl-tetrahydropyrans from arene-chromiumtricarbonyl complexes, through a similar pathway see:. Davies S.G., Donohoe T.J., and Lister M.A. Tetrahedron: Asymmetry 2 (1991) 1089
    • (1991) Tetrahedron: Asymmetry , vol.2 , pp. 1089
    • Davies, S.G.1    Donohoe, T.J.2    Lister, M.A.3
  • 20
    • 34848837144 scopus 로고    scopus 로고
    • note
    • HH = 11.0, 4.9 Hz) in 8a, tt patterns (J = 11.4-11.9, 4.3-5.1 Hz) in 7a and 9a. The equatorial proton at C4 in trans-8a exhibits a t (J = 3.0 Hz).
  • 21
    • 34848812974 scopus 로고    scopus 로고
    • note
    • 1H NMR yields, based on the characteristic signals of protons at the stereocenters, were determined using pentamethylbenzene as internal standard. The isolation of the pure products was made difficult due to the low polarities of all products.
  • 22
    • 34848821713 scopus 로고    scopus 로고
    • note
    • 4 in dichloromethane.
  • 28
    • 34848821000 scopus 로고    scopus 로고
    • note
    • 19F is: -121.6 ppm in cis-8b, and -153.0 ppm in trans-8b.
  • 30
    • 0037241494 scopus 로고    scopus 로고
    • For a nucleophilicity scale of carbon-centered nucleophiles in intermolecular reactions see: N = 2.35 for α-methyl styrene; N = 0.78 for styrene
    • For a nucleophilicity scale of carbon-centered nucleophiles in intermolecular reactions see:. Mayr H., Kempf B., and Ofial A.R. Acc. Chem. Res. 36 (2003) 66 N = 2.35 for α-methyl styrene; N = 0.78 for styrene
    • (2003) Acc. Chem. Res. , vol.36 , pp. 66
    • Mayr, H.1    Kempf, B.2    Ofial, A.R.3
  • 31
    • 34848854299 scopus 로고    scopus 로고
    • note
    • 2: 538.9945; found: 538.9939.
  • 34
    • 34848853074 scopus 로고    scopus 로고
    • note
    • Tertiary homoallenic alcohol 6e might be too crowded to trap the very first cationic intermediate. No product could be isolated from the reaction of complex 1 with this alcohol.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.