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Volumn 9, Issue 22, 2003, Pages 5664-5672

Stereoselectivity of Nitrile Oxide Cycloadditions to Chiral Allylic Fluorides: Experiment and Theory

Author keywords

Cycloaddition; Density functional calculations; Diastereoselectivity; Regioselectivity

Indexed keywords

ADDITION REACTIONS; FLUORIDE MINERALS; NITROGEN COMPOUNDS; PROBABILITY DENSITY FUNCTION;

EID: 0347088994     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200304967     Document Type: Article
Times cited : (14)

References (22)
  • 1
    • 0003907264 scopus 로고
    • (Eds.: J. T. Welch, S. Eswarakrishnan), Wiley-Interscience, New York
    • See for instance: a) Fluorine in Bioorganic Chemistry (Eds.: J. T. Welch, S. Eswarakrishnan), Wiley-Interscience, New York, 1991;
    • (1991) Fluorine in Bioorganic Chemistry
  • 2
    • 0003698431 scopus 로고    scopus 로고
    • (Eds.: T. Kitazume, T. Yamazaki), Gordon and Breach Science Publishers, Tokyo
    • b) Experimental Methods in Organic Fluorine Chemistry (Eds.: T. Kitazume, T. Yamazaki), Gordon and Breach Science Publishers, Tokyo, 1998;
    • (1998) Experimental Methods in Organic Fluorine Chemistry
  • 4
    • 0036009141 scopus 로고    scopus 로고
    • and references therein
    • M. Prakesch, D. Grée, R. Grée, Acc. Chem. Res. 2002, 35, 175, and references therein; see also F. A. Davis, P. V. N. Kasu, G. Sundarababu, H. Qi, J. Org. Chem. 1997, 62, 7546.
    • (2002) Acc. Chem. Res. , vol.35 , pp. 175
    • Prakesch, M.1    Grée, D.2    Grée, R.3
  • 8
    • 0004101860 scopus 로고
    • (Ed.: A. Padwa), Wiley, New York
    • See for instance: a) 1,3 Dipolar Cycloaddition Chemistry (Ed.: A. Padwa), Wiley, New York, 1984;
    • (1984) 1,3 Dipolar Cycloaddition Chemistry
  • 9
    • 0000629986 scopus 로고
    • (Eds.: B. M. Trost, I. Flemings), Pergamon Press, Oxford
    • b) A. Padwa, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Flemings), Vol. 4, Pergamon Press, Oxford, 1991, p. 1069;
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 1069
    • Padwa, A.1
  • 16
    • 0346005498 scopus 로고    scopus 로고
    • note
    • [11] obtained by cycloadditions on allylsilyl ethers were unsuccessful: after deprotection to the corresponding alcohols the dehydroxyfluorination was performed with DAST at low temperature on the syn and the anti isomers. In both cases the reaction afforded a complex mixture of products, including the two fluorides 5 and 6. Other methods, such as reaction of KF on corresponding tosylates, mesylates and triflates failed as well.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.