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Volumn 132, Issue 5, 2010, Pages 1685-1689

Nazarov cyclizations of an allenyl vinyl ketone with interception of the oxyallyl cation intermediate for the formation of carbon-carbon bonds

Author keywords

[No Author keywords available]

Indexed keywords

ALLENYL; BOND FORMATION; CARBON-CARBON BOND; CATION INTERMEDIATES; CYCLIZATIONS; ELECTRON-RICH ALKENES; GOOD YIELD; NAZAROV REACTION; STERIC HINDRANCES; VINYL KETONES;

EID: 76149084183     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja909073r     Document Type: Article
Times cited : (62)

References (56)
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    • (e) Hosomi, A.; Tominagi, Y. in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 593-615.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 593-615
    • Hosomi, A.1    Tominagi, Y.2
  • 24
    • 0000310315 scopus 로고    scopus 로고
    • Regarding [3 + 2] cyclizations: see refs 1f,g, 2g and (a) Hayakawa, Y.; Yokoyama, K.; Noyori, R. J. Am. Chem. Soc. 1978, 100, 1799.
    • Regarding [3 + 2] cyclizations: see refs 1f,g, 2g and (a) Hayakawa, Y.; Yokoyama, K.; Noyori, R. J. Am. Chem. Soc. 1978, 100, 1799.
  • 36
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    • and references therein
    • (c) Tius, M. A. Acc. Chem. Res. 2003, 36, 284-290, and references therein.
    • (2003) Acc. Chem. Res , vol.36 , pp. 284-290
    • Tius, M.A.1
  • 43
    • 76149118547 scopus 로고    scopus 로고
    • The structure of 8 was confirmed by X-ray crystallography.
    • The structure of 8 was confirmed by X-ray crystallography.
  • 44
    • 76149135172 scopus 로고    scopus 로고
    • The regiochemistry of the reactions was determined by analysis of 2D NMR spectra (COSY, HSQC, and HMBC) of the products.
    • The regiochemistry of the reactions was determined by analysis of 2D NMR spectra (COSY, HSQC, and HMBC) of the products.
  • 45
    • 76149135816 scopus 로고    scopus 로고
    • HF/6-31G//HF/6-311G(d, p) using Gaussian 03, Revision C.02
    • HF/6-31G//HF/6-311G(d, p) using Gaussian 03, Revision C.02.
  • 46
    • 0003218990 scopus 로고    scopus 로고
    • Cramer, C. J.; Barrows, S. E. J. Phys. Org. Chem. 2000, 13, 176. See also the earlier paper:
    • (a) Cramer, C. J.; Barrows, S. E. J. Phys. Org. Chem. 2000, 13, 176. See also the earlier paper:
  • 48
    • 0000397060 scopus 로고    scopus 로고
    • The stepwise formation of [3 + 2] products might be considered a 5-(enolendo)-exo-trig closure, a disfavored process: Baldwin, J. E.; Lusch, M. J. Tetrahedron 1982, 38, 2939.
    • The stepwise formation of [3 + 2] products might be considered a 5-(enolendo)-exo-trig closure, a disfavored process: Baldwin, J. E.; Lusch, M. J. Tetrahedron 1982, 38, 2939.
  • 49
    • 41049108081 scopus 로고    scopus 로고
    • Similar observation with furan: Rieder, C. J.; Fradette, R. J.; West, F. G. Chem. Commun. 2008, 1572.
    • Similar observation with furan: Rieder, C. J.; Fradette, R. J.; West, F. G. Chem. Commun. 2008, 1572.
  • 52
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    • NOE measurements were in accord with the stereochemical assignment
    • (c) Kwan, E. E.; Huang, S. G. Eur. J. Org. Chem. 2008, 2671. NOE measurements were in accord with the stereochemical assignment.
    • (2008) Eur. J. Org. Chem , pp. 2671
    • Kwan, E.E.1    Huang, S.G.2
  • 53
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    • A product of intramolecular cyclization involving an enol oxygen during Nazarov cyclization has been reported: Bender, J. A, Blize, A. E, Browder, C. C, Giese, S, West, F. G. J. Org. Chem. 1998, 63, 2430
    • A product of intramolecular cyclization involving an enol oxygen during Nazarov cyclization has been reported: Bender, J. A.; Blize, A. E.; Browder, C. C.; Giese, S.; West, F. G. J. Org. Chem. 1998, 63, 2430.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.