Kinetic resolution of 1-(benzofuran-2-yl)ethanols by lipase-catalyzed enantiomer selective reactions期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

Kinetic resolution of 1-(benzofuran-2-yl)ethanols by lipase-catalyzed enantiomer selective reactions

Affiliation:	1. Department of Biochemistry and Biochemical Engineering, Babeş-Bolyai University, Arany János 11, RO-3400 Cluj-Napoca, Romania;2. Institute for Organic Chemistry and Research Group for Alkaloid Chemistry of the Hungarian Academy of Sciences, Budapest University of Technology and Economics, H-1111 Budapest, Gellért tér 4, Hungary;3. Department of Agricultural Chemical Technology, Budapest University of Technology and Economics, Gellért tér 4, H-1111 Budapest, Hungary;4. Department of Chemical Engineering, Budapest University of Technology and Economics, Muegyetem Rkp 3, H-1521 Budapest, Hungary;1. Department of Nanomaterials Engineering, Chungnam National University, 79 Daehak-ro, Yuseong-gu, Daejeon 305-764, Republic of Korea;2. Graduate School of Energy Science and Technology, Chungnam National University, 79 Daehak-ro, Yuseong-gu, Daejeon 305-764, Republic of Korea;3. RASOM, Chungnam National University, 79 Daehak-ro, Yuseong-gu, Daejeon 305-764, Republic of Korea;1. Procédés, Matériaux et Energie Solaire (PROMES), UPR 8521. 7 rue du Four Solaire, 66 120 Font-Romeu Odeillo Via, France / Tecnosud – Rambla de la Thermodynamique, 66 100 Perpignan, France;2. Science des Procédés Céramiques et de Traitements de Surface (SPCTS), UMR 7315. 12 rue Atlantis, 87 068 Limoges Cedex, France;3. MISTRAS Group SA, 27 rue Magellan, Paris CEDEX 94370, France

Abstract:	Kinetic resolution of racemic 1-(benzofuran-2-yl)ethanols rac-1a–d was performed by lipase-catalyzed enantiomer selective acylation (E≫100) yielding (1R)-1-acetoxy-1-(benzofuran-2-yl)ethanes (R)-2a–d and (1S)-1-(benzofuran-2-yl)ethanols (S)-1a–d in highly enantiopure form. The degree of enantiomer selectivity for enzymatic alcoholysis/hydrolysis processes starting from racemic 1-acetoxy-1-(benzofuran-2-yl)ethane rac-2 was also tested under various conditions including supercritical CO₂ medium. Racemization-free lipase-catalyzed ethanolysis of the (1R)-1-acetoxy-1-(benzofuran-2-yl)ethanes (R)-2a–d yielded almost quantitatively the enantiopure (1R)-1-(benzofuran-2-yl)ethanols (R)-1a–d.

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