title: Ru-catalyzed asymmetric hydrogenation of δ-keto Weinreb amides: enantioselective synthesis of (+)-Centrolobine.
abstract: An efficient asymmetric hydrogenation of δ-keto Weinreb amides catalyzed by a Ru-Xyl-SunPhos-Daipen bifunctional catalyst has been achieved. This method afforded a series of enantio-enriched δ-hydroxy Weinreb amides in good yields (up to 93%) and enantioselectivities (up to 99%). This protocol was successfully applied to the synthesis of the key intermediate of (+)-Centrolobine.
authors.affiliation: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.
authors.forename: Mengmeng
authors.initials: M
authors.lastname: Zhao
authors.affiliation: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.
authors.forename: Bin
authors.initials: B
authors.lastname: Lu
authors.affiliation: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.
authors.forename: Guangni
authors.initials: G
authors.lastname: Ding
authors.affiliation: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.
authors.forename: Kai
authors.initials: K
authors.lastname: Ren
authors.affiliation: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.
authors.forename: Xiaomin
authors.initials: X
authors.lastname: Xie
authors.affiliation: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China and Shanghai Institute of Organic Chemistry, 345 Lingling Road, Shanghai 200032, China. zhaoguo@sjtu.edu.cn.
authors.forename: Zhaoguo
authors.initials: Z
authors.lastname: Zhang
mesh_terms: D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D006865:Hydrogenation; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D009942:Organometallic Compounds; D011714:Pyrans; C432457:centrolobin; D012428:Ruthenium