Organocatalytic Michael Addition/Intramolecular Julia–Kocienski Olefination for the Preparation of Nitrocyclohexenes

An asymmetric organocatalytic [3 + 3] annulation strategy based on a Michael addition/intramolecular Julia–Kocienski olefination sequence has been developed for the synthesis of 4-substituted-5-nitrocyclohex-1-ene compounds. The strategy is an alternative to the direct reluctant enantioselective Diels–Alder approach. The potential of the methodology has been demonstrated with a concise enantioselective formal synthesis of trandolapril.