β-二氟甲基化材料的立体控制合成

Stereocontrolled synthesis of beta-difluoromethylated materials.

作者信息

Nihei Takashi, Iwai Noritaka, Matsuda Tomoko, Kitazume Tomoya

机构信息

Graduate School of Bioscience & Biotechnology and Frontier Collaborative Research Center, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8501, Japan.

出版信息

J Org Chem. 2005 Jul 22;70(15):5912-5. doi: 10.1021/jo050634u.

DOI:10.1021/jo050634u

PMID:16018685

Abstract

Investigation of synthetic routes for regio- and stereocontrolled fluorinated materials with a difluoromethyl group, using ethyl bromodifluoroacetate as a starting material, is described. In particular, (E)-difluoromethylated trisubstituted olefins were prepared via the proton migration reaction catalyzed by using fluoride anion. Further, optically active beta-difluoromethyl esters were obtained by the enzymatic resolution.

摘要

描述了以溴二氟乙酸乙酯为起始原料，对具有二氟甲基的区域和立体控制氟化材料的合成路线进行的研究。特别地，通过使用氟阴离子催化的质子迁移反应制备了（E）-二氟甲基化的三取代烯烃。此外，通过酶促拆分获得了光学活性的β-二氟甲基酯。