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

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 pre dominant. The reaction proceeds by double Michael addition of the nitroalkane to the enone, followed by intramolecular aldol reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.