Preparative Organic Chemistry
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ChemInform Abstract: Highly Enantiofacial Protonation of Prochiral Lithium Enolates with Chiral β-Hydroxy Sulfoxides.
First published: 02 August 2010
Abstract
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ChemInform Abstract
Treatment of 2-alkylated enol acetates such as (I) and (III) with MeLi gives prochiral lithium enolates. They undergo an enantiofacial protonation using chiral β-hydroxy sulfoxides. Best results are obtained under the optimized conditions shown which provide 2- substituted cyclohexanone derivatives (II) and (IV) with excellent e.e.
