Categories: C-O Bond Formation >
Synthesis of β-hydroxy ethers
Epoxides can be opened under neutral conditions with alcohols and thiols in the presence of a catalytic amount of erbium(III) triflate, affording the corresponding β-alkoxy alcohols and β-hydroxy sulfides in high yields. In water, epoxide ring opening occurs to produce the corresponding diols in good yields.
R. Dalpozzo, M. Nardi, M. Oliverio, R. Paonessa, A. Procopio, Synthesis, 2009, 3433-3438.
Epoxides undergo rapid ring opening with a range of alcohols in the presence of catalytic amount of carbon tetrabromide under mild and convenient conditions to afford the corresponding β-alkoxy alcohols and 1,2-diols in high yields with high regioselectivity.
J. S. Yadav, B. V. S. Reddy, K. Harikishan, Ch. Madan, A. V. Narsaiah, Synthesis, 2005, 2897-2900.
Epoxides can be cleaved in a regio- and stereoselective manner under neutral conditions with water, alcohols and acetic acid in the presence of catalytic amounts of decatungstocerate(IV) ion, affording the corresponding diols, β-alkoxy and β-acetoxy alcohols in high yields.
V. Mirkhani, S. Tangestaninejad, B. Yadollahi, L. Alipanah, Tetrahedron, 2003, 59, 8213-8218.