Nickel Catalyzed Regio-, Diastereo-, and Enantioselective Cross-Coupling of 3,4-Epoxyalcohol with Aryl Iodides.

The first catalytic, regioselective cross-coupling of 3,4-epoxyalcohol with aryl iodides is reported. The combination of NiCl2·DME and a newly developed C2-symmetric oxazoline ligand plays a key role in selective ring opening of several 3,4-epoxy alcohols at the C4 position. This general protocol furnishes a new type of enantioenriched 4,4-diaryl alkane which also incorporates an additional 1,3-diol that can be easily transformed to a variety of functional groups. The products are formed with excellent regioselectivity (>99:1), diastereoselectivity (up to 99:1), and enantiopurity (up to >99.9% ee).