Portal de Periódicos da CAPES

Diisopropyl tartrate (E)-γ-(dimethylphenylsilyl)allylboronate, a chiral allylic alcohol β-carbanion equivalent for the enantioselective synthesis of 2-butene-1,4-diols from aldehydes

1990; Elsevier BV; Volume: 31; Issue: 52 Linguagem: Inglês

10.1016/s0040-4039(00)97300-3

1873-3581

William Roush, Paul Grover,

Analytical Chemistry and Chromatography

An enantioselective synthesis of 4-substituted (E)-2-buten-1,4-diols is described. The method involves the reaction of aldehydes with the chiral PhMe2Si- substituted allylboronate3 followed by epoxidation (dimethyl dioxirane) and acid catalyzed Petersen rearrangement of the intermediate epoxysilanols.