American Chemical Society
ol8b01323_si_001.pdf (5.73 MB)

Palladium-Catalyzed Benzylic Phosphorylation of Diarylmethyl Carbonates

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journal contribution
posted on 2018-05-25, 02:15 authored by Akihiro Matsude, Koji Hirano, Masahiro Miura
A palladium-catalyzed benzylic substitution of tert-butyl diarylmethyl carbonates with a pinacol-derived H-phosphonate proceeds to deliver the corresponding benzylic phosphorylated products in good yields. Moreover, the asymmetric synthesis is possible via a Pd/(Rp,Rp)-(S)-Mandyphos-catalyzed kinetic resolution–DYKAT (dynamic kinetic asymmetric transformation) sequence, and optically active α-chiral diarylmethylphosphonates are obtained with synthetically useful yields and enantiomeric ratios (up to 50% and 92:8 er).