Organic Letters
Organic Letters
5 years ago

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

Nickel Catalyzed Regio-, Diastereo-, and Enantioselective Cross-Coupling of 3,4-Epoxyalcohol with Aryl Iodides
Hisashi Yamamoto, Amit Banerjee
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).

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02076

DOI: 10.1021/acs.orglett.7b02076

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