title: Organocatalytic approach to polysubstituted piperidines and tetrahydropyrans.
abstract: Polysubstituted piperidines and tetrahydropyrans are synthesized from aldehydes and two classes of trisubstituted nitroolefins via an O-TMS protected diphenylprolinol catalyzed domino Michael addition/aminalization (or acetalization) process. This approach allows formation of four contiguous stereocenters in the piperidine or tetrahydropyran ring in one step with excellent enantioselectivity.
authors.affiliation: Department of Chemistry, Fudan University, Shanghai 200433, China.
authors.forename: You
authors.initials: Y
authors.lastname: Wang
authors.forename: Shaolin
authors.initials: S
authors.lastname: Zhu
authors.forename: Dawei
authors.initials: D
authors.lastname: Ma
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D006900:Hydroxylation; D008958:Models, Molecular; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis*; D011714:Pyrans / Q000138:chemical synthesis*
chemical_list: D000447:Aldehydes; D010880:Piperidines; D011714:Pyrans