An Efficient Synthesis of exo/endo‐Hydroxylated Cyclohexenones by Thiol/Amine‐Mediated Tandem Aldol–[2,3]‐Sigmatropic Rearrangement: Amine‐Dependent Complementary Regioselectivity

Motofumi Miura; Toshinori Nakakita; Masaharu Toriyama; Shigeyasu Motohashi

Index: 10.1002/ajoc.201800081

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Abstract

exo/endo‐Hydroxylated cyclohexenones are essential synthetic intermediates for a variety of biologically active compounds. However, methods that lead to efficient and selective preparation of exo/endo‐hydroxylated cyclohexenones remain to be established. Herein, we report the practical and scalable synthesis of exo/endo‐hydroxylated cyclohexenones from readily available 2,6‐diketosulfoxides. We demonstrate that endo and exo geometric isomers of hydroxylated cyclohexenones can be obtained by simple modification of the reaction conditions.