Auxiliary controlled singlet-oxygen ene reactions of cyclohexenes

W Fudickar, K Vorndran, T Linker

Index: Fudickar, Werner; Vorndran, Katja; Linker, Torsten Tetrahedron, 2006 , vol. 62, # 46 p. 10639 - 10646

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Citation Number: 15

Abstract

The photooxygenation of homochiral cyclohexene ketals, which are easily available from 2- cyclohexenone and l-tartrates, affords hydroperoxides and after reduction the corresponding allylic alcohols in good yields and high regioselectivities. This can be rationalized by electronic repulsions in a perepoxide intermediate and provides evidence for unfavorable 1, 3 diaxial interactions with a dioxolane oxygen atom. Only low stereoselectivities were ...