Highly efficient double enantioselection by lipase-catalyzed transesterification of (R,S)-carboxylic acid vinyl esters with (RS)-1-phenylethanol |
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| Institution: | 1. Department of Analytical Chemistry, Voronezh State University, University Square 1, 394006 Voronezh, Russia;2. Department of Chemical Reaction Engineering, Friedrich-Alexander-University Erlangen-Nürnberg, Egerlandstr. 3, D-91058 Erlangen, Germany;3. Department of Chemistry, Institute of Inorganic and Applied Chemistry, University of Hamburg, Martin-Luther-King Platz 6, D-20146 Hamburg, Germany;1. Faculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie St., 50-383 Wrocław, Poland;2. Wrocław University of Technology, Institute of Inorganic Technology, 27 Wybrzeże Wyspiańskiego, 50-370 Wrocław, Poland;1. Department of Chemistry and Industrial Chemistry, University of Pisa, Via G. Moruzzi 3, 56124 Pisa, Italy;2. Department of Molecular Sciences and Nanosystems, University Ca’ Foscari of Venice, Dorsoduro 2137, 30123 Venice, Italy;3. Department of Chemical Sciences, University of Padua, Via Marzolo 1, 35131 Padua, Italy;4. ICCOM CNR, via G. Moruzzi 1, 56124 Pisa, Italy;5. Department of Civil and Industrial Engineering, Largo Lucio Lazzarino 2, 56126 Pisa, Italy;6. Department of Industrial Chemistry “Toso Montanari”, University of Bologna, Viale Risorgimento 4, 41036 Bologna, Italy;1. College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu, 215123, PR China;2. The Key Lab of Health Chemistry and Molecular Diagnosis of Suzhou, PR China;3. Department of Quartermaster Engineering, Jilin University, No. 5333, Xi''an Road, Changchun 130062, PR China;1. School of Engineering, University of Guelph, Guelph, Ontario N1G 2W1, Canada;2. Department of Chemical and Materials Engineering, University of Alberta, Edmonton, Alberta, T6G 2V4, Canada |
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| Abstract: | Transesterification of the title compounds using lipase B from Candida antarctica in toluene afforded the corresponding esters in good to excellent diastereomeric excess. (R)-2-Phenylpropionic acid-(R)-1-phenethyl ester 4 was isolated in 45% yield and 64% de after 2.5 h, whereas (R)-2-phenylbutyric acid-(R)-1-phenethyl ester 5 was obtained in 40% yield and 56% de after 35 h. A single recrystallization from n-hexane gave 4 with 98% de. In all reactions CAL-B showed excellent enantioselectivity (E >100) toward (RS)-1-phenylethanol and moderate enantioselectivity (E∼10) toward both carboxylic acid vinyl esters. |
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