Organocatalytic enantioselective desymmetrization of cyclic enones via phosphine promoted [3+2] annulations.
Phosphine catalyzed enantioselective [3+2] cyclizations on 4-substituted 2,6-diarylidenecyclohexanones and 2,4-diarylidene-bicyclo[3.1.0]hexan-3-ones take place with high diastereo- and enantioselectivity levels. The process affords spirocyclic compounds with excellent stereochemical control of up to five stereogenic centres.
Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Centre de Recherche de Gif. 1, av. de la Terrasse, 91198 Gif-sur-Yvette, France.
Nathalie
N
Pinto
Pascal
P
Retailleau
Arnaud
A
Voituriez
Angela
A
Marinetti
D002384:Catalysis; D003500:Cyclization; D003512:Cyclohexanones / Q000138:chemical synthesis / Q000737:chemistry*; D006588:Hexanones / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D010720:Phosphines / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D003512:Cyclohexanones; D006588:Hexanones; D010720:Phosphines; D013141:Spiro Compounds; C044646:phosphine