Preparation of the four stereoisomers of 3-bromo-2-butanol or their acetates via lipase-catalysed resolutions of the racemates derived from dl- or meso-2,3-butanediol |
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| Affiliation: | 1. School of Biotechnology, Department of Biochemistry, Royal Institute of Technology (KTH), AlbaNova University Center, SE-106 91 Stockholm, Sweden;2. Department of Natural Sciences, Mid Sweden University, SE-851 70 Sundsvall, Sweden;1. A.M. Prokhorov General Physics Institute, Vavilov st. 38, 119991 Moscow, Russia;2. University of Rostock, Institute of Physics, Albert-Einstein-Str. 23-24, 18051 Rostock, Germany;1. Faculty of Chemistry and Chemical Technology, Department of Chemistry, Moldova State University, 60 Mateevici Street, MD 2009 Chisinau, Republic of Moldova;2. Institute of Applied Physics, Academy of Sciences, 5 Academiei Street, MD 2028 Chisinau, Republic of Moldova;1. Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan;2. Japan JEOL Ltd., Akishima, Tokyo 196-8558, Japan;3. Sugashima Marine Biological Laboratory, Nagoya University, Toba, Mie 517-0004, Japan;4. Takehara Marine Science Station, Hiroshima University, Takehara, Hiroshima 725-0024, Japan;1. Institute for Solar Energy Systems, School of Physics and Engineering, Sun Yat-Sen University, 5th Floor, C Block, Building of Engeneering, 132 Wai Huan Dong Road, Higher Education Mega Center, Guangzhou, Guangdong, PR China;2. State Key Laboratory of PV Science and Technology, Trina Solar, No. 2 Trina Road, Trina PV Park, New District, Changzhou, Jiangsu, PR China;3. Jiangsu Collaborative Innovation Center of Photovoltaic Science and Engineering, Changzhou University, No. 1 Gehu Road, Changzhou, Jiangsu Province, PR China;4. Shun De SYSU Institute for Solar Energy, No. 1, Deshengdong Road, Shunde, Guangdong, PR China |
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| Abstract: | 
The four stereoisomeric 3-bromo-2-butanols and/or their acetates were prepared via lipase-catalysed kinetic resolution by hydrolyses of the acetates of the (±)-syn- and (±)-anti-3-bromo-2-butanols, or via esterifications of the alcohols. The diastereomeric bromoacetates were obtained by syntheses from the dl- and meso-2,3-butanediols, respectively. On a preparative scale, the four stereoisomers, either as the free alcohols or as their acetates, were obtained in >95% ee, and in 35–40% yield (based on the starting racemates). |
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