Abstract
Acylation of meso-2,3-dimethylbutane-1,4-diol with vinyl acetate in the presence of porcine pancreatic lipase (PPL) leads to the dextrorotatory monoacetate of the above diol with enatiomeric excess (ee) 58—64%. Absolute configuration of this scalemic specimen was determined by its sequential transformation to levorotatory lasiol, a metabolite of the Lasius ants. Partial hydrolysis of the corresponding meso-diacetate, mediated by PPL or by the Pseudomonas sp. lipase affords the monoacetate of opposite configuration with ee 72—86%, a formal intermediate in the synthesis of (3S,4R)-faranal. Other microbial lipases used are distinctive in low chemoselectivity.
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Vasil"ev, A.A., Vielhauer, O., Engman, L. et al. Enzymatic dissymmetrization of meso-2,3-dimethylbutane-1,4-diol and its diacetate. Synthesis of scalemic (–)-lasiol. Russian Chemical Bulletin 51, 481–487 (2002). https://doi.org/10.1023/A:1015512419633
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DOI: https://doi.org/10.1023/A:1015512419633