Nickel Catalyzed Regio-, Diastereo-, and Enantioselective Cross-Coupling of 3,4-Epoxyalcohol with Aryl Iodides
作者:Amit Banerjee、Hisashi Yamamoto
DOI:10.1021/acs.orglett.7b02076
日期:2017.8.18
The first catalytic, regioselective cross-coupling of 3,4-epoxyalcohol with aryl iodides is reported. The combination of NiCl2 center dot DME and a newly developed C-2-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).