Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 7, Pages 3387-3396Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo502667x
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Funding
- Deutsche Forschungsgemeinschaft (DFG) [SPP1179, BE 998/11-1, GR 3461/2-1]
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The combination of an asymmetric organocatalytic aldol reaction with a subsequent biotransformation toward a one-pot-like process for the synthesis of (R)-pantolactone, which to date is industrially produced by a resolution process, is demonstrated. This process consists of an initial aldol reaction catalyzed by readily available L-histidine followed by biotransformation of the aldol adduct by an alcohol dehydrogenase without the need for intermediate isolation. Employing the industrially Attractive starting material isobutanal, a chemoenzymatic three-step process without intermediate purification is established allowing the synthesis of (R)-pantolactone in an overall yield of 55% (three steps) and high enantiomeric excess of 95%.
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