Article ID Journal Published Year Pages File Type
5278231 Tetrahedron Letters 2008 4 Pages PDF
Abstract

Highly diastereoselective aldol-type condensations induced by the chiral magnesium enolate of tert-butyl p-tolyl sulfinyl acetate were performed with optically pure alkyl or hydroxy α-substituted aldehydes. The addition of chiral α-sulfinyl acetate to various aldehydes, α-substituted or not, results mainly with a syn stereochemistry of the two newly created stereocenters. Applications were investigated for the synthesis of syn and trans 1,2-diol models and polysubstituted precursor for natural products.

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Physical Sciences and Engineering Chemistry Organic Chemistry
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