Rhodium-mediated insertion of CF3-substituted carbenoid into O-H: An efficient method for the synthesis of α-trifluoromethylated alkoxy- and aryloxyacetic acid derivatives

作者: Guo-qiang Shi , Zhi-yao Cao , Wei-ling Cai

DOI: 10.1016/0040-4020(95)98698-H

关键词: MoleculeCarbenoidYield (chemistry)RhodiumChemistryOrganic chemistryAlkoxy groupMedicinal chemistryDiazoInsertion reactionPhenols

摘要: CF3-substituted diazo compound 2 undergoes a facile rhodium carbenoid mediated O-H insertion reaction with variety of alcohols and phenols to afford the title compounds in good yield. Use as synthetic precursors for other fluorinated molecules is exemplified by transformation product 3b into β, β-difluoro- α-ketoester 5 α-hydroxyketone 8.

参考文章(32)
義郎 小林, 日本化学会, Robert Filler, Biomedicinal aspects of fluorine chemistry Kodansha , Elsevier Biomedical Press , Sole distributors for the U.S.A. and Canada, Elsevier Science Pub. Co.. ,(1982)
Seetha Eswarakrishnan, John T. Welch, Fluorine in bioorganic chemistry Wiley. ,(1991)
Robert Filler, Lev M. Yagupolskii, Yoshiro Kobayashi, Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications ,(1993)
H. Stegemeyer, R. Meister, U. Hoffmann, W. Kuczynski, Induced smectic C* phases Liquid Crystals. ,vol. 10, pp. 295- 310 ,(1991) , 10.1080/02678299108026277
Enrique Aller, Geoffrey G. Cox, David J. Miller, Christopher J. Moody, Diastereoselectivity in the OH insertion reactions of rhodium carbenoids derived from phenyldiazoacetates of homochiral alcohols Tetrahedron Letters. ,vol. 35, pp. 5949- 5952 ,(1994) , 10.1016/S0040-4039(00)78227-X
V.G. Andreev, A.F. Kolomiets, A.V. Fokin, [3,3]-Sigmatropic rearrangements of fluorocarbanions Journal of Fluorine Chemistry. ,vol. 56, pp. 259- 269 ,(1992) , 10.1016/S0022-1139(00)81173-2
Geoffrey G. Cox, David J. Miller, Christopher J. Moody, Eric-Robert H.B. Sie, Janusz J. Kulagowski, Rhodium-carbenoid mediated O-H insertion reactions. O-H insertion vs. H-abstraction and effect of catalyst Tetrahedron. ,vol. 50, pp. 3195- 3212 ,(1994) , 10.1016/S0040-4020(01)81117-0
Guoqiang Shi, Yuanyao Xu, A facile synthesis of α-trifluorodiazo compounds Journal of Fluorine Chemistry. ,vol. 46, pp. 173- 178 ,(1990) , 10.1016/S0022-1139(00)81567-5