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Determination of absolute configuration of 2-methyl-1-(o-tolyl)naphthalene and the related axially chiral biaryls
Authors:Lijie SunWei-Min Dai
Institution:Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China
Abstract:An enantiomerically enriched sample (84.3% ee) of (aS)-2-methyl-1-(((o-triisopropylsilyl)oxy)methyl)phenyl]naphthalene was produced via catalytic asymmetric Suzuki-Miyaura cross-coupling using an atropisomeric naphthamide-derived phosphine (A2phos) as the chiral ligand. After one recrystallization, enantiopurity of the biaryl product was improved to 98.9% ee and its absolute configuration was determined by X-ray crystal structural analysis. Through chemical transformations, the (aS)-enantiomers of 1-(o-hydroxymethyl)phenyl]-2-methylnaphthalene, 1-(o-chloromethyl)phenyl]-2-methylnaphthalene, and 2-methyl-1-(o-tolyl)naphthalene were obtained. Several other chiral biaryls were synthesized and stereochemically assigned.
Keywords:Asymmetric Suzuki-Miyaura cross-coupling  Atropisomeric naphthamide  Chemical resolution  Chiral biaryl  Chiral phosphine
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