Cross-Metathesis approach to a,w-Bifunctional Compounds from Methyl Oleate and cis-2-Butene-1,4-diol

The cross metathesis (CM) of methyl oleate (1) and cis-2-butene-1,2-diol (2) was investigated to access alpha, omega-bifunctional compounds. The optimal CM conditions involve Stewart-Grubbs catalyst at 0 °C, delivering CM product 3 in excellent yield. 3 was converted, in a single step and in >90% yields, to alcohol 7, aldehyde 8, and olefin 10, the useful synthetic intermediates for many specialty chemicals, including PA11 precursor. A tandem CM/isomerization process was also demonstrated for the first time.