A concise synthesis of (R)- and (S)-α-alkyl isoserines from d- and l-malic acids |
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| Institution: | 1. Federal University of Rio Grande do Sul (UFRGS), Engineering School, Laboratory of Polymeric Materials (LAPOL), P.O. Box 15010, 91501-970 Porto Alegre, Brazil;2. University of Birmingham, Chemical Engineering School, B15 2TT Birmingham, England, United Kingdom;3. HySA Systems Competence Centre, SAIAMC, University of the Western Cape, Private Bag X17, Bellville 7535, Cape Town, South Africa |
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| Abstract: | A simple and diastereoselective method for the synthesis of (R)- and (S)-α-alkyl isoserines has been developed in four steps starting from commercially available d- and l-malic acid, respectively. This approach features stereocontrolled alkylation of 2-(2-tert-butyl-5-oxo-1,3-dioxolan-4-yl)acetic acid and proceeds through a methylcarbamate via a Curtius rearrangement. |
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