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Volumn , Issue 8, 2000, Pages 1483-1488

Inter- and intramolecular crotyltitanation of acetals: A novel and effective route to three- to five-membered vinylcycloalkanes and bicyclic fused compounds

Author keywords

Acetals; Cyclizations; Synthetic methods; Titanium

Indexed keywords

ACETAL DERIVATIVE; CYCLOALKANE DERIVATIVE; VINYL DERIVATIVE;

EID: 0034018460     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(200004)2000:8<1483::aid-ejoc1483>3.0.co;2-y     Document Type: Article
Times cited : (5)

References (46)
  • 1
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    • (Eds.: B. M. Trost, I. Fleming, C. W. Heathcock), Pergamon Press, New York
    • [1a] I. Fleming, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, C. W. Heathcock), Pergamon Press, New York, 1991, Vol. 2, p 563.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 563
    • Fleming, I.1
  • 32
    • 0343048870 scopus 로고    scopus 로고
    • Similarly to the reactions of acetals with other allylic metals, no reaction occurred between 1 and 2 under the Lewis acid-free conditions
    • Similarly to the reactions of acetals with other allylic metals, no reaction occurred between 1 and 2 under the Lewis acid-free conditions.
  • 33
    • 85088000020 scopus 로고    scopus 로고
    • [2]
    • [2].
  • 36
    • 84988113098 scopus 로고
    • [16a] For the synthesis of 20-22, see J. C. Stowell, D. R. Keith, Synthesis 1979, 132-133. [16b] For the synthesis of 23 see S. F. Reed, J. Org. Chem. 1965, 30, 1663-1665. [16c] For the synthesis of 24 see: D. R. Goldberg, J. A. Hansen, R. J. Giguere, Tetrahedron Lett. 1993, 34, 8003-8006.
    • (1979) Synthesis , pp. 132-133
    • Stowell, J.C.1    Keith, D.R.2
  • 37
    • 0001480582 scopus 로고
    • [16a] For the synthesis of 20-22, see J. C. Stowell, D. R. Keith, Synthesis 1979, 132-133. [16b] For the synthesis of 23 see S. F. Reed, J. Org. Chem. 1965, 30, 1663-1665. [16c] For the synthesis of 24 see: D. R. Goldberg, J. A. Hansen, R. J. Giguere, Tetrahedron Lett. 1993, 34, 8003-8006.
    • (1965) J. Org. Chem. , vol.30 , pp. 1663-1665
    • Reed, S.F.1
  • 38
    • 0027138119 scopus 로고
    • [16a] For the synthesis of 20-22, see J. C. Stowell, D. R. Keith, Synthesis 1979, 132-133. [16b] For the synthesis of 23 see S. F. Reed, J. Org. Chem. 1965, 30, 1663-1665. [16c] For the synthesis of 24 see: D. R. Goldberg, J. A. Hansen, R. J. Giguere, Tetrahedron Lett. 1993, 34, 8003-8006.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 8003-8006
    • Goldberg, D.R.1    Hansen, J.A.2    Giguere, R.J.3
  • 39
    • 85087998901 scopus 로고    scopus 로고
    • [6]
    • [6].
  • 40
    • 0342342168 scopus 로고
    • Academic, New York.
    • The stereochemical assignments for compounds 25-29 and 33-35 were established based on the NOE experiments and/or are in accordance with the literature data, see: [18a] W. Brugel, Nuclear Magnetic Resonance and Chemical Structure, Vol. 1., Academic, New York. 1965. [18b] R. Barlet, R. Le Goaller, C. Gey, Can. J. Chem. 1981, 59, 621.
    • (1965) Nuclear Magnetic Resonance and Chemical Structure , vol.1
    • Brugel, W.1
  • 41
    • 0343484792 scopus 로고
    • The stereochemical assignments for compounds 25-29 and 33- 35 were established based on the NOE experiments and/or are in accordance with the literature data, see: [18a] W. Brugel, Nuclear Magnetic Resonance and Chemical Structure, Vol. 1., Academic, New York. 1965. [18b] R. Barlet, R. Le Goaller, C. Gey, Can. J. Chem. 1981, 59, 621.
    • (1981) Can. J. Chem. , vol.59 , pp. 621
    • Barlet, R.1    Le Goaller, R.2    Gey, C.3
  • 44
    • 37049098975 scopus 로고
    • This regiochemical feature is identical to that observed for the intermolecular crotyltitanation of aldehydes using similar cyclic dienes, see: Y. Kobayashi, K. Umeyama, F. Sato, J. Chem. Soc., Chem. Commun. 1984, 621-623.
    • (1984) J. Chem. Soc., Chem. Commun. , pp. 621-623
    • Kobayashi, Y.1    Umeyama, K.2    Sato, F.3
  • 45
    • 0343048867 scopus 로고    scopus 로고
    • Unfortunately, we could not determine the stereochemistry for the compound 35a
    • Unfortunately, we could not determine the stereochemistry for the compound 35a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.