메뉴 건너뛰기




Volumn , Issue 14, 2002, Pages 2064-2074

Asymmetric tandem additions to chiral 2,3-dihydronaphthyloxazolines: Synthesis of the triptoquinone/triptinin a ring system

Author keywords

Alkyllithiums; Chiral oxazolines; Conjugate additions; Deoxygenation; Ring closing metathesis; Tetralones; Triflates

Indexed keywords

CATALYSTS; SYNTHESIS (CHEMICAL);

EID: 0036398438     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34373     Document Type: Article
Times cited : (18)

References (27)
  • 1
    • 0001428655 scopus 로고    scopus 로고
    • For reviews on the use of chiral oxazolines in synthesis, see: (a) Meyers, A. I. J. Heterocycl. Chem. 1998, 35, 991. (b) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297. (c) Reumann, M.; Meyers, A. I. Tetrahedron 1985, 41, 837.
    • (1998) Heterocycl. Chem. , vol.35 , pp. 991
    • Meyers, A.I.J.1
  • 2
    • 0028157516 scopus 로고
    • For reviews on the use of chiral oxazolines in synthesis, see: (a) Meyers, A. I. J. Heterocycl. Chem. 1998, 35, 991. (b) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297. (c) Reumann, M.; Meyers, A. I. Tetrahedron 1985, 41, 837.
    • (1994) Tetrahedron , vol.50 , pp. 2297
    • Gant, T.G.1    Meyers, A.I.2
  • 3
    • 0342738155 scopus 로고
    • For reviews on the use of chiral oxazolines in synthesis, see: (a) Meyers, A. I. J. Heterocycl. Chem. 1998, 35, 991. (b) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297. (c) Reumann, M.; Meyers, A. I. Tetrahedron 1985, 41, 837.
    • (1985) Tetrahedron , vol.41 , pp. 837
    • Reumann, M.1    Meyers, A.I.2
  • 16
    • 2142837610 scopus 로고    scopus 로고
    • note
    • Compound 12 was prepared as described in the experimental.
  • 18
    • 2142678528 scopus 로고    scopus 로고
    • note
    • Attempts were made to use a vinyl bromide into the tandem product below. However, the electrophilic step in the tandem addition failed. Presumably, the azaenolate, formed upon the addition of the 2-lithiopropene, is too basic and causes elimination of HBr from 1,3-dibromobut-3-ene (Scheme 11).
  • 20
    • 2142852153 scopus 로고    scopus 로고
    • note
    • The yield of this reaction was dependent upon the quality of the catalyst (purchased from Strem Chemical Company) as evidenced by its often dark color.
  • 24
    • 85088335683 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of 32-34 and 38 are included in the supplementary material.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.