Abstract

The reaction of (2 S, S S)- α-(1-hydroxyethyl)vinyl sulfoxide with alkyl radicals and tributyltin hydride gave the addition-hydrogenation products with high diastereoselectivity, whereas (2 R, S S)- α-(1-hydroxyethyl)vinyl sulfoxide gave no products under similar conditions. An important role of intramolecular hydrogen bonding for the diastereoselectivity as well as the reactivity toward alkyl radicals is discussed.

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