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Volumn 64, Issue 44, 2008, Pages 10123-10131

Metal-mediated dearomatization leading to 2-azaspiro[4.5]decanes via tandem nucleophilic aromatic addition-Horner-Wadsworth-Emmons olefination-oxidative demetalation sequences

Author keywords

Arene ruthenium; Dearomatization; Horner Wadsworth Emmons reaction; Oxidative demetalation; Spirocyclization

Indexed keywords

ALDEHYDE DERIVATIVE; AROMATIC COMPOUND; CYCLOHEXANE DERIVATIVE; DECANE; HETEROCYCLIC COMPOUND; LACTAM DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; RUTHENIUM COMPLEX; SODIUM DERIVATIVE; SPIRO COMPOUND;

EID: 51349167604     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.08.024     Document Type: Article
Times cited : (10)

References (44)
  • 1
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    • 6-arene)metal chemistry:
    • 6-arene)metal chemistry:
  • 3
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    • Abel E.W., Stone F.G.A., and Wilkinson G. (Eds), Elsevier Science, Oxford pp 979-1038
    • Semmelhack M.F. In: Abel E.W., Stone F.G.A., and Wilkinson G. (Eds). Comprehensive Organometallic Chemistry II Vol. 12 (1995), Elsevier Science, Oxford pp 979-1038
    • (1995) Comprehensive Organometallic Chemistry II , vol.12
    • Semmelhack, M.F.1
  • 24
    • 51349098552 scopus 로고    scopus 로고
    • note
    • +, found 355.0506. The structure of i was also definitively established by X-ray crystallography.{A figure is presented}
  • 25
    • 51349110654 scopus 로고    scopus 로고
    • note
    • A similar rearrangement has been observed in complexes related to 2, see Refs. 5b,c.
  • 27
    • 51349115705 scopus 로고    scopus 로고
    • This type of nucleophilic oxidative demetalation has been reported for other metal dienyl and metal allyl systems. For examples, see:
    • This type of nucleophilic oxidative demetalation has been reported for other metal dienyl and metal allyl systems. For examples, see:
  • 38
    • 51349164510 scopus 로고    scopus 로고
    • note
    • Details of this structure will be published elsewhere.
  • 39
    • 51349124517 scopus 로고    scopus 로고
    • note
    • 2Br was also recovered from these reactions.
  • 41
    • 51349154333 scopus 로고    scopus 로고
    • note
    • The relative stereochemistry in 23a,b has been tentatively assigned as indicated consistent with initial nucleophilic addition from the metal-free face of the cyclohexadienyl ligand followed by stereoselective [3,3] sigmatropic rearrangement. Attempts to definitively establish the stereochemistry via 2D NMR (NOESY) were thwarted by the absence of diagnostic correlations.
  • 44
    • 51349095249 scopus 로고    scopus 로고
    • Herz W., Kirby G.W., Moore R.E., Steglich W., and Tamm Ch. (Eds), Springer, New York, NY pp 125-165
    • Walser-Volken P., and Tamm Ch. In: Herz W., Kirby G.W., Moore R.E., Steglich W., and Tamm Ch. (Eds). Progress in the Chemistry of Organic Natural Products Vol. 67 (1996), Springer, New York, NY pp 125-165
    • (1996) Progress in the Chemistry of Organic Natural Products , vol.67
    • Walser-Volken, P.1    Tamm, Ch.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.