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Volumn 2, Issue 6, 2000, Pages 823-826

Stereoselectivity of methyl aryldiazoacetate cyclopropanations of 1,1-diarylethylene. Asymmetric synthesis of a cyclopropyl analogue of tamoxifen

Author keywords

[No Author keywords available]

Indexed keywords

ANTIESTROGEN; BENZENE DERIVATIVE; DIRHODIUM TETRAKIS(S (N DODECYLBENZENESULFONYL)PROLINATE); DIRHODIUM TETRAKIS(S-(N-DODECYLBENZENESULFONYL)PROLINATE); DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ORGANOMETALLIC COMPOUND; PROLINE; TAMOXIFEN;

EID: 0034704637     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005563u     Document Type: Article
Times cited : (51)

References (19)
  • 18
    • 0003972881 scopus 로고
    • John Wiley & Sons: New York
    • A possible explanation for this difference in effect may come from Hammet studies we have carried out for competition reactions of substituted styrenes with various carbenoids (ref 9). In these studies, we found that vinyldiazoacetates and phenyldiazoacetates (jn contrast to simple diazoacetates) display considerable selectivity in competition studies with various styrenes and the reactivity correlates well with a σ+ scale rather than a σ scale. This would suggest that the benzylic carbon of the styrene has some carbocation character in the transition state of the cyclopropanation and is stabilized by resonance through to the aromatic substituent. Consequently, it is reasonable that the methoxy group would have a more significant effect on the diastereoselectivity of the 1,1-diarylethylene cyclopropanation than a nitro group. The influence of the nitro group would be primarily through a polar effect rather than a resonance effect and would be largely independent of aromatic ring orientation. For a general discussion, see: Hine, J. In Structural Effects on Equilibra in Organic Chemistry: John Wiley & Sons: New York, 1975; pp 55-105.
    • (1975) Structural Effects on Equilibra in Organic Chemistry , pp. 55-105
    • Hine, J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.