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Abstract
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.
Supplementary materials
Title
Electronic supporting information
Description
This supporting information include:
1) Experimental sectioin
2) An alternative route to Methyl 11-aminoundecanoate from Methyl 11-
hydroxyundecanoate
3) Metathesis catalyst screening
4) Additional studies on allyl alcohol isomerization to aldehyde
5) Ruthenium-catalyzed isomerization of Methyl (E)-11-hydroxyundec-9-enoate to
Methyl 11-oxoundecanoate
6) Cross-metathesis / allyl alcohol isomerization – one-pot procedure
7) 1H and 13C NMR spectra
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