title: An organocatalytic approach to enantiomerically enriched α-arylcyclohexenones and cyclohexanones.
abstract: The presence of a p-nitrophenyl group converts acetone into an excellent and versatile nucleophile in organocatalytic processes, able to react with α,β-unsaturated aldehydes affording β-substituted α-arylcyclohexenones via a Michael reaction/aldol reaction/dehydration sequence, which occurs in good yields, ee up to 96% and complete diastereoselectivity. The resulting compounds are excellent synthons for the diastereoselective preparation of a variety of synthetically useful polysubstituted cyclohexanones and derivatives.
authors: Department of Organic Chemistry, Universidad Autónoma de Madrid, Cantoblanco, 28049.
authors: Sara
authors: S
authors: Duce
authors: María
authors: M
authors: Jorge
authors: Inés
authors: I
authors: Alonso
authors: José Luis
authors: JL
authors: García Ruano
authors: M Belén
authors: MB
authors: Cid
mesh_terms: D000096:Acetone / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D003512:Cyclohexanones; D000096:Acetone