title: Carboxy-directed asymmetric hydrogenation of α-alkyl-α-aryl terminal olefins: highly enantioselective and chemoselective access to a chiral benzylmethyl center.
abstract: A carboxy-directed asymmetric hydrogenation of α-alkyl-α-aryl terminal olefins was developed by using a chiral spiro iridium catalyst, providing a highly efficient approach to the compounds with a chiral benzylmethyl center. The carboxy-directed hydrogenation prohibited the isomerization of the terminal olefins, and realized the chemoselective hydrogenation of various dienes. The concise enantioselective syntheses of (S)-curcudiol and (S)-curcumene were achieved by using this catalytic asymmetric hydrogenation as a key step.
authors.affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China.
authors.forename: Shuang
authors.initials: S
authors.lastname: Yang
authors.forename: Shou-Fei
authors.initials: SF
authors.lastname: Zhu
authors.forename: Na
authors.initials: N
authors.lastname: Guo
authors.forename: Song
authors.initials: S
authors.lastname: Song
authors.forename: Qi-Lin
authors.initials: QL
authors.lastname: Zhou
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D007495:Iridium / Q000737:chemistry; D008968:Molecular Conformation; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001593:Benzyl Compounds; D005233:Fatty Alcohols; D010636:Phenols; D012717:Sesquiterpenes; C454669:curcudiol; D007495:Iridium; C086829:alpha-curcumene