Journal
ORGANIC LETTERS
Volume 15, Issue 15, Pages 3872-3875Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol401606x
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Funding
- Spanish Ministerio de Ciencia e Innovacion (MICINN) [CTQ 2012-24237]
- MICINN
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A straightforward chemoenzymatic synthesis of enantiopure 4-alkyl-3-methyl-3,4-dihydrolsocoumarins through a ketoreductase-catalyzed one-pot dynamic reductive kinetic resolution is reported. E. coli/ADH-A cells have shown outstanding diastereo- and enantioselectivity toward the bioreduction of a series of racemic ketones, with the use of anion exchange resins or triethylamine being compatible in the same aqueous reaction medium. The so-obtained enantiopure alcohols were subsequently cyclized in acid media affording the corresponding lactones in good to excellent conversions (72-96%) and excellent selectivities (dr >= 99:1 and ee >99%).
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