Synthesis of (R)-1-[(S)-2-(Diphenylphosphino)ferrocenyl] ethyldi(3,5-dimethylphenyl)phosphine
Published 2011 · Zhu Hong-jun
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Abstract
(R)-1-Ferrocenylethyldimethylamine(Ⅲ) was synthesized from acetylferrocene via a hydrogenative amination catalyzed with Pd/C and chemical resolution with(R)-(+)-tartaric acid.Lithiation of Ⅲ with n-BuLi and following phosgenation with ClPPh2 provided(R)-N,N-dimethyl-(S)-1-(2-diphenylphosphinoferrocenyl)ethylamine(Ⅳ).(R)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldi(3,5-dimethylphenyl)phosiphine(Ⅷ) was obtained by treatment of Ⅳ with freshly prepared di(3,5-dimethylphenyl)phosphine through a configurationally retentive displacement in an overall yield of 19.5% calculated from acetylferrocene,the ee of which was about 95% according to the chiral HPLC analysis.
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