Deracemization of α-monosubstituted Cyclopentanone (cas 120-92-3)s in the presence of a TADDOL-type host molecule

Add time:09/03/2019    Source:sciencedirect.com

Racemic α-monosubstituted cyclopentanones were converted to optically active forms by a thermodynamically controlled deracemization using TADDOL-type host molecule 1 in alkaline aqueous MeOH. The efficiency of this conversion was strongly influenced by the ratio of the solvent components (H2O/MeOH) and the functionality and architecture of the α-side-chain on the cyclopentanones. For example, (R)-2-(2-benzyloxyethyl)cyclopentanone (9) was obtained in 89% yield with 97% ee using a 7:3 mixture of H2O/MeOH as the solvent. X-ray analytical studies were also carried out and disclosed the nature of this chiral molecular recognition process in the solid phase.

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