One-pot diastereoselective synthesis of 2-acyl-4-nitrocyclohexanol derivatives in aqueous medium

Abstract

The reaction of primary nitroalkanes with conjugated enones, in water and in the presence of K2CO3 as base, allows the synthesis of 2-acyl-4-nitrocyclohexanol derivatives in which the diastereoisomer (±)-(1S∗,2R∗,5R) is highly predominant. The reaction proceeds by double Michael addition of the nitroalkane to the enone, followed by intramolecular aldol reaction.