title: Camphor-based Schiff base ligand SBAIB: an enantioselective catalyst for addition of phenylacetylene to aldehydes.
abstract: A series of Schiff base ligands were synthesized from (1R)-camphor. Under the optimal conditions, (+)-SBAIB-a, 10 was found to be an excellent catalyst for the enantioselective addition of phenylacetylene to various aldehydes without utilizing either achiral additives or Ti(O(i)Pr)(4). This approach yielded (R)-propargylic alcohols in extremely high yields (up to 99%) and excellent enantioselectivities (up to 92%). The corresponding (S)-propargylic alcohols were synthesized in good to high enantioselectivities (up to 91%) and excellent yields (up to 99%) using (-)-SBAIB-a, 41.
authors.affiliation: Department of Chemistry, National Dong Hwa University, Soufeng, Hualien 974, Taiwan, Republic of China.
authors.forename: Ramalingam
authors.initials: R
authors.lastname: Boobalan
authors.forename: Chinpiao
authors.initials: C
authors.lastname: Chen
authors.forename: Gene-Hsian
authors.initials: GH
authors.lastname: Lee
mesh_terms: D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D001892:Camphanes / Q000737:chemistry*; D002164:Camphor / Q000737:chemistry*; D002384:Catalysis; D008024:Ligands; D008958:Models, Molecular; D015394:Molecular Structure; D012545:Schiff Bases / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001892:Camphanes; D008024:Ligands; D012545:Schiff Bases; C044736:phenylacetylene; D002164:Camphor; D000114:Acetylene