AI Article Synopsis
- Silyl enol ether 9 successfully reacted with benzaldehyde under the influence of O-allyl trifluorobenzyl cinchonium hydrofluoride (20 mol % catalyst), resulting in a single syn-product 8 with a yield of 76% and an enantiomeric excess (ee) of 80%.
- Further purification via recrystallization improved the ee to 95%, and the final product was transformed into valuable ester intermediates through a Baeyer-Villiger reaction.
Article Abstract
Cinchona phase-transfer catalysts (PTC) were developed for glycolate aldol reactions to give differentially protected 1,2-diol products. Silyl enol ether 9 reacted to generate benzhydryl-protected products. O-Allyl trifluorobenzyl cinchonium hydrofluoride CN-4 (20 mol %) catalyzed the addition of 9 to benzaldehyde to give 8 as a single syn-product in 76% yield and 80% ee. Recrystallization enriched the product to 95% ee, and a Baeyer-Villiger reaction transformed the product into useful ester intermediates. [reaction: see text]
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| http://dx.doi.org/10.1021/ol051096a | DOI Listing |
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