title: Concise asymmetric synthesis of (+)-CP-99,994 and (+)-L-733,060 via efficient construction of homochiral syn-1,2-diamines and syn-1,2-amino alcohols.
abstract: An efficient asymmetric synthesis of human NK-1 SP receptor antagonists (+)-CP-99,994 and (+)-L-733,060 was achieved starting from a common chiral intermediate (5). Our route featured the SmI2-induced reductive coupling of N-tert-butanesulfinyl imine (7) with aldehyde (6) as the key step as well as pivotal transformations of the anti-1,2-amino alcohol thus obtained to homochiral syn-1,2-amino alcohol and syn-1,2-diamine for the asymmetric synthesis of 2,3-disubstituted piperidines.
authors.affiliation: Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433.
authors.forename: Run-Hua
authors.initials: RH
authors.lastname: Liu
authors.forename: Kai
authors.initials: K
authors.lastname: Fang
authors.forename: Bing
authors.initials: B
authors.lastname: Wang
authors.forename: Ming-Hua
authors.initials: MH
authors.lastname: Xu
authors.forename: Guo-Qiang
authors.initials: GQ
authors.lastname: Lin
mesh_terms: D000605:Amino Alcohols / Q000737:chemistry*; D003959:Diamines / Q000737:chemistry*; D006900:Hydroxylation; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000605:Amino Alcohols; D003959:Diamines; D010880:Piperidines; C080755:3-(2-methoxybenzylamino)-2-phenylpiperidine; C103788:3-((3,5-bis(trifluoromethyl)phenyl)methyloxy)-2-phenylpiperidine