title: A Helical Polyphenylacetylene Having Amino Alcohol Moieties Without Chiral Side Groups as a Chiral Ligand for the Asymmetric Addition of Diethylzinc to Benzaldehyde.
abstract: One-handed helical polyphenylacetylenes having achiral amino alcohol moieties, but no chiral side groups, were synthesized by the helix-sense-selective copolymerization of an achiral phenylacetylene having an amino alcohol side group with a phenylacetylene having two hydroxyl groups. Since the resulting helical copolymers were successfully utilized as chiral ligands for the enantioselective alkylation of benzaldehyde with diethylzinc, we can conclude that the main-chain chirality based on the one-handed helical conformation is useful for the chiral catalysis of an asymmetric reaction for the first time. The enantioselectivities of the reaction were controlled by the optical purities of the helical polymer ligands. In addition, the polymer ligands could be easily recovered by precipitation after the reaction.
authors.affiliation: Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin, China.
authors.forename: Lijia
authors.initials: L
authors.lastname: Liu
authors.affiliation: Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin, China.
authors.forename: Qing
authors.initials: Q
authors.lastname: Long
authors.affiliation: Graduate School of Science and Technology, Niigata University, Niigata, Japan.
authors.forename: Toshiki
authors.initials: T
authors.lastname: Aoki
authors.affiliation: Graduate School of Science and Technology, Niigata University, Niigata, Japan.
authors.forename: Geng
authors.initials: G
authors.lastname: Zhang
authors.affiliation: Graduate School of Science and Technology, Niigata University, Niigata, Japan.
authors.forename: Takashi
authors.initials: T
authors.lastname: Kaneko
authors.affiliation: Graduate School of Science and Technology, Niigata University, Niigata, Japan.
authors.forename: Masahiro
authors.initials: M
authors.lastname: Teraguchi
authors.affiliation: Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin, China.
authors.forename: Chunhong
authors.initials: C
authors.lastname: Zhang
authors.affiliation: Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin, China.
authors.forename: Yudan
authors.initials: Y
authors.lastname: Wang
mesh_terms: D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000605:Amino Alcohols; D001547:Benzaldehydes; D009942:Organometallic Compounds; C044736:phenylacetylene; D000114:Acetylene; C454811:diethylzinc; C032175:benzaldehyde
keywords: achiral amino alcohol; chiral polymer ligand; one-handed helical main-chain; poly(substituted acetylene)