Enzymatic Synergism in the Synthesis of β-Keto Esters

作者: Catalina Wiśniewska , Dominik Koszelewski , Małgorzata Zysk , Szymon Kłossowski , Anna Żądło

DOI: 10.1002/EJOC.201500676

关键词:

摘要: Reaction of alcohols with ethyl and tert-butyl acetoacetate catalyzed by a combination commercially available enzymes is shown to be convenient method for the preparation range acetoacetic acid derivatives. Systematic studies proved that two or more enhances yield reaction. Application selected enzyme mixture enzymatic transesterification various β-keto esters provided respective products in excellent yields up 96 % quantitative within 24 48 hours, respectively. The presented methodology simple mild, can used prepare acetoacetates from primary secondary alcohols.

参考文章(64)
Simon Patching, Vasyl Andrushko, Natalia Andrushko, Stereoselective synthesis of drugs and natural products John Wiley & Sons, Inc.. ,(2013) , 10.1002/9781118596784
MASAYUKI SATO, NORIO KANUMA, TETSUZO KATO, Synthesis of N-Acylacetoacetamide using 2, 2, 6-Trimethyl-1, 3-dioxin-4-one Chemical & Pharmaceutical Bulletin. ,vol. 30, pp. 1315- 1321 ,(1982) , 10.1248/CPB.30.1315
Kwang-Wook Kim, Boyoung Song, Min-Young Choi, Mahn-Joo Kim, Biocatalysis in ionic liquids: markedly enhanced enantioselectivity of lipase. Organic Letters. ,vol. 3, pp. 1507- 1509 ,(2001) , 10.1021/OL015824F
Christopher R. Holmquist, Eric J. Roskamp, A selective method for the direct conversion of aldehydes into .beta.-keto esters with ethyl diazoacetate catalyzed by tin(II) chloride Journal of Organic Chemistry. ,vol. 54, pp. 3258- 3260 ,(1989) , 10.1021/JO00275A006
Michael Butters, Christopher D. Davies, Mark C. Elliott, Joseph Hill-Cousins, Benson M. Kariuki, Li-ling Ooi, John L. Wood, Stuart V. Wordingham, Synthesis and stereochemical determination of batzelladine C methyl ester Organic and Biomolecular Chemistry. ,vol. 7, pp. 5001- 5009 ,(2009) , 10.1039/B914744F
D.W. Hutchinson, Metal chelators as potential antiviral agents Antiviral Research. ,vol. 5, pp. 193- 205 ,(1985) , 10.1016/0166-3542(85)90024-5
Joel L. Kaar, Anita M. Jesionowski, Jason A. Berberich, Roger Moulton, Alan J. Russell, Impact of Ionic Liquid Physical Properties on Lipase Activity and Stability Journal of the American Chemical Society. ,vol. 125, pp. 4125- 4131 ,(2003) , 10.1021/JA028557X
Yoshisato Tezuka, Tetsuya Ogura, Shinichi Kawaguchi, π-Allylie Coordination of Ethyl Acetoacetate to Palladium(II) Bulletin of the Chemical Society of Japan. ,vol. 42, pp. 443- 446 ,(1969) , 10.1246/BCSJ.42.443