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.
Department of Organic Chemistry. Universidad Autónoma de Madrid , Cantoblanco 28049, Madrid, Spain.
Eduardo
E
Rodrigo
José Luis
JL
García Ruano
M Belén
MB
Cid
D002384:Catalysis; D053138:Cyclohexenes / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D053138:Cyclohexenes; D007211:Indoles; D009574:Nitro Compounds; C052035:trandolapril