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. Author manuscript; available in PMC: 2020 Mar 9.
Published in final edited form as: Nat Catal. 2019 Sep 9;2(10):882–888. doi: 10.1038/s41929-019-0336-1

Fig. 5.

Fig. 5

Development of proof of concept catalytic enantioselective C4- and C5-arylations. Reaction conditions: 7 (1.0 equiv), s-BuLi (1.2 equiv), (+)-sp surrogate (0.3 equiv), diisopropylbispidine (1.3 equiv), Et2O, –78 °C, 8 h, then Zn(OAc)2 (C4-arylation) or ZnCl2 (C5-arylation), THF (1.2 equiv), –78→20 °C, 1 h, then removal of volatiles, then PhBr (0.7 equiv), Pd2dba3 (2.5 mol%), ligand (5 mol%), toluene, 80 °C, 17 h. a Using (+)-sp instead of the (+)-sp surrogate.