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Volumn 24, Issue 13, 2005, Pages 3182-3191

Theoretical investigation on the mechanisms of the PtCl 2-mediated cycloisomerization of polyfunctionalized 1,6-enynes. 2. Propargylic carboxylates

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; CARBOXYLATION; CATALYSIS; COMPLEXATION; COMPUTATIONAL METHODS; MOLECULAR DYNAMICS; PLATINUM COMPOUNDS; REACTION KINETICS;

EID: 21744442268     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om050134r     Document Type: Article
Times cited : (70)

References (77)
  • 6
    • 0000449988 scopus 로고    scopus 로고
    • Fürstner, A., Ed.; Springer-Verlag: Berlin
    • (b) Mori, M. In Topics in Organometallic Chemistry; Fürstner, A., Ed.; Springer-Verlag: Berlin, 1998; Vol. 1, p 133.
    • (1998) Topics in Organometallic Chemistry , vol.1 , pp. 133
    • Mori, M.1
  • 57
    • 23144448976 scopus 로고    scopus 로고
    • note
    • 3 = -1.24°.
  • 58
    • 23144460936 scopus 로고    scopus 로고
    • note
    • 2 in the reactant complex (+0.04 vs +0.17 in 11, Table S3; see the Supporting Information) would account for a less favorable electrostatic interaction with nucleophilic carbonyl oxygen and a higher energy transition state for acyl migration step as the first step.
  • 59
    • 23144446450 scopus 로고    scopus 로고
    • note
    • Optimized structures for this mechanistic proposal are given in the Supporting Information.
  • 60
    • 23144463804 scopus 로고    scopus 로고
    • note
    • 9
  • 61
    • 23144466100 scopus 로고    scopus 로고
    • note
    • 3 = -2.07°.
  • 64
    • 23144449619 scopus 로고    scopus 로고
    • note
    • This mechanism has also been proposed by other authors, (a) For Rh(I)-catalyzed cycloisomerization of enynes for the preparation of functionalized lactams, see ref 5c.
  • 66
    • 23144434437 scopus 로고    scopus 로고
    • note
    • 2, see ref 6d.
  • 67
    • 0033952688 scopus 로고    scopus 로고
    • (d) For cycloisomerization with [CpRu(MeCN)3] [PF6], see: Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714-715.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 714-715
    • Trost, B.M.1    Toste, F.D.2
  • 68
    • 23144451285 scopus 로고    scopus 로고
    • note
    • A detailed analysis of the overall mechanism, which also accounts for the preferential abstraction of hydrogen from the trans allylic position in the intermediate 21, is provided as part of the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.