title: Cyclohydrocarbonylation-based strategy toward poly-substituted piperidines.
abstract: Convenient accesses to enantiomerically pure 2-, 2,3-, 2,6-, 2,3,6-substituted piperidines and 1,4-substituted indolizine are described. At first, indium-mediated aminoallylation and -crotylation of aldehydes with (R)-phenylglycinol or (1R,2S)-1-amino-2-indanol gave homoallylamines with high stereocontrol. Then, these products, submitted to a Rh(I)-catalyzed hydroformylative cyclohydrocarbonylation, afforded perhydrooxazolo[3,2-a]piridines whose oxazolidines are opened with nucleophiles. Finally, the removal of the chiral auxiliaries delivered the enantiomerically pure piperidines.
authors.affiliation: Dipartimento Farmaco Chimico Tecnologico, Università degli Studi di Siena, Via A. Moro 2, 53100 Siena, Italy.
authors.forename: Giada
authors.initials: G
authors.lastname: Arena
authors.forename: Nicolas
authors.initials: N
authors.lastname: Zill
authors.forename: Jessica
authors.initials: J
authors.lastname: Salvadori
authors.forename: Nicolas
authors.initials: N
authors.lastname: Girard
authors.forename: André
authors.initials: A
authors.lastname: Mann
authors.forename: Maurizio
authors.initials: M
authors.lastname: Taddei
mesh_terms: D006844:Hydrocarbons, Cyclic / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis*
chemical_list: D006844:Hydrocarbons, Cyclic; D010880:Piperidines