Chiral nonracemic C2-symmetry biphenyls by desymmetrization of 6,6′,2,2′-tetramethoxy-1,1′-biphenyl

Add time:07/13/2019    Source:sciencedirect.com

Regioselective bromination of the title biphenyl 1 at the 3 and 3′ positions and simultaneous desymmetrization of the biphenyl has been achieved. Metal–halide exchange at the 3,3′ positions facilitated the introduction of functional groups in good yield. Regioselective reduction was obtained by using (CH3)3SiI, L-Selectride and HI according to the functional groups on the biphenyls. Resolution of 6,6′,2,2′-tetramethoxy-3,3′-dimethyl-1,1′-biphenyl 3 was achieved by its conversion to the corresponding phosphorothioamidate diastereomers of the (S)-(−)-α-methylbenzylamine. The absolute configuration of (M)-(+)-3 was confirmed by X-ray analysis of the corresponding diastereomer.

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