title: Enantioselective synthesis of 2,6-cis-disubstituted tetrahydropyrans via a tandem catalytic asymmetric hydrogenation/oxa-Michael cyclization: an efficient approach to (-)-centrolobine.
abstract: A highly efficient one-pot process via a tandem reaction of catalytic asymmetric hydrogenation and oxa-Michael cyclization for the synthesis of 2,6-cis-disubstituted tetrahydropyrans has been developed (ee up to 99.9%, cis/trans-selectivity up to 99:1). This method provides a concise route to (-)-centrolobine (68.8% yield, three steps).
authors.affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China. jhxie@nankai.edu.cn
authors.forename: Jian-Hua
authors.initials: JH
authors.lastname: Xie
authors.forename: Lu-Chuan
authors.initials: LC
authors.lastname: Guo
authors.forename: Xiao-Hui
authors.initials: XH
authors.lastname: Yang
authors.forename: Li-Xin
authors.initials: LX
authors.lastname: Wang
authors.forename: Qi-Lin
authors.initials: QL
authors.lastname: Zhou
mesh_terms: D002384:Catalysis; D003500:Cyclization; D006865:Hydrogenation; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D011714:Pyrans; C432457:centrolobin