Tetrahedron letters

Stereoselective hydrogenation of α-sulfinyl radical generated from alkyl radical addition to α-(1-hydroxyethyl) vinyl sulfoxide

N Mase, S Wake, Y Watanabe, T Toru

Index: Mase, Nobuyuki; Wake, Shutaro; Watanabe, Yoshihiko; Toru, Takeshi Tetrahedron Letters, 1998 ,  vol. 39,  # 31  p. 5553 - 5556

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Citation Number: 19

Abstract

The reaction of (2S, SS)-α-(1-hydroxyethyl) vinyl sulfoxide with alkyl radicals and tributyltin hydride gave the addition-hydrogenation products with high diastereoselectivity, whereas (2R, SS)-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.