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Volumn 68, Issue 20, 2003, Pages 7722-7732

Samarium(II)-promoted radical spirocyclization onto an aromatic ring

Author keywords

[No Author keywords available]

Indexed keywords

SPIROCYCLIZATION;

EID: 0141766927     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034767w     Document Type: Article
Times cited : (59)

References (98)
  • 79
  • 85
    • 0141695556 scopus 로고    scopus 로고
    • note
    • An NOE experiment of epoxide 69 derived from 39a showed reasonable correlations as shown below. Furthermore, treatment of a mixture of 38a and 39a with DBU afforded the corresponding isomerized product 70 as a single isomer in 79% yield. For the determination of relative configurations of other spirocycles, see the Supporting Information. (Equation Presented)
  • 90
    • 0141695554 scopus 로고    scopus 로고
    • note
    • Approach of the phenyl ring from the less hindered side (the opposite side of the axial protons) affords cyclized products with the observed stereochemistry. (Equation Presented)
  • 91
    • 0141695555 scopus 로고    scopus 로고
    • note
    • 4 afforded separable primary alcohols 71 and 72. The relative configuration of 71 was determined by NOE analysis. Furthermore, hydrogenation of the mixture of 46 and 47 in the presence of catalytic Pd/C gave the corresponding spiro-[4.5]decane derivative 73 as a single isomer. (Equation Presented)
  • 92
    • 0141472293 scopus 로고    scopus 로고
    • note
    • Recently, Reissig and co-workers reported the related ketyl radical cyclization onto the aromatic ring activated by a methoxy or cyano group.15c In all cases, the position meta to the methoxy or cyano group is more reactive than the other positions. (Equation Presented)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.