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Volumn 3, Issue 5, 2001, Pages 671-674

A double ring closing metathesis reaction in the rapid, enantioselective synthesis of NK-1 receptor antagonists

Author keywords

[No Author keywords available]

Indexed keywords

1 OXO 7 AZASPIRODECANE; 1-OXO-7-AZASPIRODECANE; HETEROCYCLIC COMPOUND; NEUROKININ 1 RECEPTOR; SPIRO COMPOUND;

EID: 0035826378     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006958g     Document Type: Article
Times cited : (77)

References (33)
  • 4
    • 0032580376 scopus 로고    scopus 로고
    • For recent reviews of the metathesis reaction in synthesis, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
    • (1998) Tetrahedron , vol.54 , pp. 4413
    • Grubbs, R.H.1    Chang, S.2
  • 8
    • 0002673788 scopus 로고    scopus 로고
    • Alkene metathesis in organic synthesis
    • (e) Alkene Metathesis in Organic Synthesis; Furstner, A., Ed. Top. Organomet. Chem. 1998, 1.
    • (1998) Top. Organomet. Chem. , pp. 1
    • Furstner, A.1
  • 20
    • 0041906508 scopus 로고    scopus 로고
    • note
    • Isomer ratios quoted were determined by hplc analysis (Zorbax Eclipse XDB-C8 0.46 x 25 cm column). Yields are for the isolated compounds after column chromatography.
  • 26
    • 0041405387 scopus 로고    scopus 로고
    • note
    • Despite screening a range of reaction conditions (temperature, solvent, additives and other catalysts), this selectivity could not be improved.
  • 29
    • 0043162336 scopus 로고
    • Monte Carlo searches were performed to ensure that all low-energy conformations had been included in the calculations
    • Chang, G.; Guida, W. C.; Still, W. C. Monte Carlo searches were performed to ensure that all low-energy conformations had been included in the calculations. J. Am. Chem. Soc. 1989, 111, 4379.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 4379
    • Chang, G.1    Guida, W.C.2    Still, W.C.3
  • 30
    • 0042407726 scopus 로고    scopus 로고
    • note
    • Relative ratios were determined by HPLC analysis.
  • 31
    • 0042908555 scopus 로고    scopus 로고
    • note
    • It is possible that 15a and 15b are formed in significant quantities but that their further cyclization is faster than that for the dihydrofurans 14a and 14b. However, the consistent ratio of the two product isomers throughout the reaction (70:30 at all conversions) does not support this.
  • 32
    • 0041405383 scopus 로고    scopus 로고
    • note
    • No acyclic compounds were observed during this reaction.
  • 33
    • 0041405382 scopus 로고    scopus 로고
    • note
    • Details of modeling studies on the intermediate compounds are provided in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.