Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 25, Issue 4, Pages 941-946Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.0c00557
Keywords
cascade reaction; biocatalysis; transaminase; alcohol dehydrogenase; ketoreductase
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Funding
- Austrian COMET Program by the Austrian Federal Ministry of Transport, Innovation and Technology (BMVIT) [862766]
- Austrian Federal Ministry of Digital and Economic Affairs (BMDW) [862766]
- State of Styria (Styrian Funding Agency SFG) [862766]
- Banco Santander-Fundacion San Pablo-CEU
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A biocatalytic cascade for producing tert-butyl ((2R,4R)-2-methyltetrahydro-2H-pyran-4-yl)carbamate 6 has been demonstrated at a multikilogram scale. The process involves resolving a racemic ketone by selectively reducing the undesired ketone and then catalyzing enantioselective transamination to form the desired amine. The product is recovered after Boc protection in the aqueous reaction.
A biocatalytic cascade to produce tert-butyl ((2R,4R)-2-methyltetrahydro-2H-pyran-4-yl)carbamate 6 has been demonstrated at the multikilogram scale. In this reaction, a racemic ketone is resolved by reducing the undesired ketone using a ketone reductase (KRED). The reduction is stereospecific for the 2-position of substrate (2S)-ketone leaving the (2R)-ketone unreacted. After the (2S)-ketone has been depleted, a transaminase is added to catalyze the enantioselective transamination of the ketone, resulting in formation of the (2R, 4R)-amine 6. The product is recovered from the aqueous reaction after Boc protection.
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