title: Diastereoconvergent synthesis of trans-5-hydroxy-6-substituted-2-piperidinones by addition-cyclization-deprotection process.
abstract: A diastereoselective one-pot approach to access trans-5-hydroxy-6-substituted-2-piperidinones by an addition-cyclization-deprotection process has been developed, in which the stereogenic center at the C-6 position was solely controlled by α-OTBS group. The utility of this transformation is demonstrated by the asymmetric synthesis of the enantiomer of (-)-CP-99,994.
authors.affiliation: Department of Chemistry and Institute of Biomedical Sciences, Fudan University , 220 Handan Road, Shanghai 200433, P.R. China.
authors.forename: Chang-Mei
authors.initials: CM
authors.lastname: Si
authors.forename: Wei
authors.initials: W
authors.lastname: Huang
authors.forename: Zhen-Ting
authors.initials: ZT
authors.lastname: Du
authors.forename: Bang-Guo
authors.initials: BG
authors.lastname: Wei
authors.forename: Guo-Qiang
authors.initials: GQ
authors.lastname: Lin
mesh_terms: D003500:Cyclization; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry; D010881:Piperidones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D010880:Piperidines; D010881:Piperidones; C080755:3-(2-methoxybenzylamino)-2-phenylpiperidine; C043384:2-piperidone