Regiocontrolled Opening of Cyclic Ethers Using Dimethylboron Bromide

The cleavage of various cyclic ethers (3- to 7-membered rings) was achieved under very mild conditions using dimethylboron bromide to afford the corresponding bromo alcohols. In particular, 2-substituted tetrahydrofurans were regioselectively cleaved by a predominantly SN2-type mechanism favoring the formation of primary vs. secondary bromides. Dimethylboron bromide also cleaved chemoselectively substituted tetrahydrofurans in the presence of functional groups such as acyclic ethers, silyl ethers, esters, amides, ketones, etc. © 1987, American Chemical Society. All rights reserved.

Duke Scholars

Author Michael J. Therien Chemistry