Categories: C-O Bond Formation >
Synthesis of ortho esters
Primary, secondary and electron-deficient tertiary alcohols react rapidly with ketene dimethyl acetal to form mixed ortho esters, without catalysts and under solvent-free conditions. 1,2-Diols yield bis(mixed ortho esters), rather than cyclic ortho esters.
K. L. Cosgrove, R. P. McGeary, Synlett, 2008, 2425-2428.
A wide variety of functionalized orthoesters can be prepared under mild and green electrochemical conditions from easily accessible dithiane derivatives.
A. D. Garcia, M. C. Leech, A. Petti, C. Denis, I. C. A. Goodall, A. P. Dobbs, K. Lam, Org. Lett., 2020, 22, 3875-3878.
Bicyclo orthoesters and amide acetals were prepared from the corresponding triols or diethanolamines using α,α-difluoroalkylamines. The reactions proceeded under mild conditions.
S. Tange, T. Fukuhara, S. Hara, Synthesis, 2008, 3219-3222.