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note
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3 (25.8 mg, 0.05 mmol) and (R)-2,2′-di(2-amino-5-chlorophenoxy)-1,1′-binaphthyl (7d) (53.7 mg, 0.10 mmol) were mixed in a pyrex Schlenk tube at room temperature under nitrogen atmosphere. To the mixture was added freshly distilled and well-degassed toluene (10 mL), and this solution was stirred for 30 min at that temperature. Then, phenylacetylene (2a) (153.2 mg, 1.5 mmol) and N-benzylidenebenzeneamine (1a) (181.2 mg, 1.0 mmol) were added, and the mixture was stirred at room temperature for 24 h. The resulting mixture was then filtered through a pad of Celite and purified by neutral silica gel column chromatography (eluent: hexane/EtOAc), to give the desired propargylamine (3a) in 73% yield (206.9 mg). The enantiomeric purity was determined by HPLC on chiral column (OD-H) (82% ee, R).
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