Determination of absolute configuration of 2-methyl-1-(o-tolyl)naphthalene and the related axially chiral biaryls |
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Authors: | Lijie SunWei-Min Dai |
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Institution: | Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China |
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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. |
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Keywords: | Asymmetric Suzuki-Miyaura cross-coupling Atropisomeric naphthamide Chemical resolution Chiral biaryl Chiral phosphine |
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