Regioselective Ring-Cleavage Reaction of Tetrahydrofurans and Tetrahydropyrans Accompanied by Carbon–Carbon Bond Formation
作者:Akira Oku、Yukio Homoto、Toshiro Harada
DOI:10.1246/cl.1986.1495
日期:1986.9.5
Various 2-substituted tetrahydrofurans and tetrahydropyrans were cleaved regioselectively accompanied by a simultaneous carbon–carbon bond formation at the highly substituted α carbon atom by using the reagent system of titanium tetrachloride and ally- (or alkynyl-)silanes.
We have established the first catalytic C-C and C-N bond formation reactions of O-heterocycles (e.g., tetrahydrofuran, phthalane, and lactone derivatives) using iron bichloride as a catalyst in the presence of TMSN3 or allylsilanes accompanied by the ring opening of O-heterocycles. The reactions smoothly proceeded at room temperature to give the corresponding primary saturated alcohols from the 2-substituted tetrahydrofurans, ortho-substituted benzyl alcohols from phthalanes, and saturated carboxylic acids from lactones in high yields.