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

Abstract

exo/endo-Hydroxylated cyclohexenones are essential synthetic intermediates for av ariety of biologically active compounds. However,m ethods that lead to efficient and selectivep reparation of exo/endo-hydroxylated cyclohexenones remain to be established. Herein, we report the practical and scalables ynthesis 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.