title: Diastereomeric aziridine carbinol catalyzed enantioselective arylation reaction: toward the asymmetric synthesis of both enantiomers of chiral 3-aryl phthalide.
abstract: The diastereomeric aziridine carbinols are applied, respectively, as efficient chiral ligand in the catalysis of asymmetric arylation and sequential arylation-lactonization cascade. The two diastereomers, which are facilely synthesized from the same chiral source, function as pseudo enantiomers in arylation of aromatic aldehydes providing the different enantiomers of the diarylmethanols with almost the same excellent enantioselectivities. The arylation method is also carried out in tandem with lactonization process to afford a concise synthetic approach to both enantiomers of optically active 3-aryl phthalide.
authors.affiliation: The College of Chemistry and Molecular Engineering, Zhengzhou University , No. 75 Daxue Road, Zhengzhou, Henan Province 450052, P. R. China.
authors.forename: Xixi
authors.initials: X
authors.lastname: Song
authors.forename: Yuan-Zhao
authors.initials: YZ
authors.lastname: Hua
authors.forename: Jing-Guo
authors.initials: JG
authors.lastname: Shi
authors.forename: Ping-Ping
authors.initials: PP
authors.lastname: Sun
authors.forename: Min-Can
authors.initials: MC
authors.lastname: Wang
authors.forename: Junbiao
authors.initials: J
authors.lastname: Chang
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001388:Aziridines; D001572:Benzofurans; C082022:phthalide