One-Pot Synthesis of Optically Active Cyanohydrin Acetates from Aldehydes via Quinidine-Catalyzed Transhydrocyanation Coupled with Lipase-Catalyzed Kinetic Resolution in Organic Solvent

doi:10.1246/BCSJ.65.111

Paper

One-Pot Synthesis of Optically Active Cyanohydrin Acetates from Aldehydes via Quinidine-Catalyzed Transhydrocyanation Coupled with Lipase-Catalyzed Kinetic Resolution in Organic Solvent

Published 1992 · M. Inagaki, A. Hatanaka, M. Mimura

Bulletin of the Chemical Society of Japan

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Abstract

A novel one-pot synthetic method was developed for the preparation of optically active cyanohydrin acetates. Racemic cyanohydrins were generated from aldehydes and acetone cyanohydrin by quinidine-catalyzed transhydrocyanation, and the resulting cyanohydrins 2a–j were then acetylated by lipase in a stereoselective manner using isopropenyl acetate as an acylating regent. A variety of aldehydes 1a–j were successfully transformed into the corresponding cyanohydrin acetates 3a–j having 47–95% e.e. without isolating the unstable cyanohydrins 2. Moreover, the reversible nature of base-catalyzed transhydrocyanation allows for in situ racemization of the unreacted cyanohydrins and concurrent kinetic resolution by lipase enabled the preparation of (S)-3b–d with 40–82% e.e. in more than 50% yield. Polymer-supported cinchona alkaloid was also used as a catalyst for this one-pot reaction and showed the comparable chemical and optical yield to that for the soluble monomeric alkaloid. The insoluble polymer and lipase w...

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This one-pot method enables the preparation of optically active cyanohydrin acetates from aldehydes with 47-95% e.e. in over 50% yield, using quinidine-catalyzed transhydrocyanation and lipase-catalyzed kinetic

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

One-Pot Synthesis of Optically Active Cyanohydrin Acetates from Aldehydes via Quinidine-Catalyzed Transhydrocyanation Coupled with Lipase-Catalyzed Kinetic Resolution in Organic Solvent

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References

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Citations

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