Cascade Biotransformations via Enantioselective Reduction, Oxidation, and Hydrolysis: Preparation of (R)-未-Lactones from 2-Alkylidenecyclopentanones
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文摘
The first cascade biotransformation involving enantioselective reduction of a C鈺怌 double bond, Baeyer鈥揤illiger oxidation, and lactone hydrolysis was developed as a green and sustainable tool for synthesizing enantiopure 未-lactones. One-pot cascade biotransformations were achieved with Acinetobacter sp. RS1 containing a novel enantioselective reductase and an enantioselective lactone hydrolase and Escherichia coli coexpressing cyclohexanone monooxygenase and glucose dehydrogenase, converting easily available 2-alkylidenecyclopentanones 1鈥?b>2 into the corresponding valuable flavors and fragrances (R)-未-lactones 5鈥?b>6 in high ee. The one-pot synthesis is better than the reported two-step preparation. This concept is useful in developing other redox cascades with the substrates containing C鈺怌 double bond.