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Volumn 40, Issue 51, 1999, Pages 8979-8983

Diastereoselective synthesis of 2-isoxazolines via silaketal tethered 1,3-dipolar cycloadditions

Author keywords

4,5 Dihydroisoxazoles; Cycloadditions; Diastereo selection; Isoxazolines; Nitrile oxides; Silyl nitronates

Indexed keywords

2 ISOXAZOLINE DERIVATIVE; NITRILE; NITRO DERIVATIVE;

EID: 0033579588     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01916-4     Document Type: Article
Times cited : (10)

References (29)
  • 7
    • 0001497447 scopus 로고
    • Curran, D. P., Ed.; JAI Press: Greenwich
    • (c) Curran, D. P. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich, 1988; Vol. 1, pp. 129-189.
    • (1988) Advances in Cycloaddition , vol.1 , pp. 129-189
    • Curran, D.P.1
  • 21
    • 85038140049 scopus 로고    scopus 로고
    • note
    • Those allylic alcohols not commercially available were prepared by the addition of Grignard reagents to the corresponding unsaturated aldehydes. Nitroalcohols were prepared from the condensation of nitromethane with the corresponding aldehydes.
  • 22
    • 85038142195 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis of a sample of the reaction mixture showed a complete disappearance of the resonances attributed to the alkene function accompanied by the appearance of those attributed to the 2-isoxazoline product.
  • 23
    • 85038146286 scopus 로고    scopus 로고
    • note
    • 13C NMR). The assignment of all resonances was supported by COSY and HMQC cross peak correlations. Stereochemistry was established on the basis of NOE experiments. Because each silaketal is derived from racemic alcohols, both diastereomers 8a and 9a are obtained as a mixture of epimers at C-2 in equal proportions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.