Tetrahedron

Iron/copper promoted fragmentation reactions of α-alkoxy hydroperoxides: Regio-and stereocontrolled formation of olefin-containing macrolides

SL Schreiber, B Hulin, W Liew

Index: Schreiber, Stuart L.; Hulin, Bernard; Liew, Wai-Fong Tetrahedron, 1986 ,  vol. 42,  # 11  p. 2945 - 2950

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Citation Number: 35

Abstract

Several new examples of iron/copper mediated fragmentation reactions of hydroperoxides are reported. The regio-and stereochemistry of olefin formation is in accord with a model that takes into account the preferred conformations of the radical intermediate and potential olefin products. In combination with group selective peroxyketalization reactions, several stereocontrolled syntheses of olefin containing macrolides have been achieved.