Synthesis of cyclic allyl vinyl ethers using Pt(II)-catalyzed isomerization of oxo-alkynes

Several alkynyl epoxides and one alkynyl allyl alcohol were isomerized to cyclic allyl vinyl ethers (3,4-dihydro-2H-1,4-oxazines) using PtCl2 as the catalyst. Three of these allyl vinyl ethers were converted to 2-hydroxymorpholine derivatives by hydrolysis and two were converted to piperidine derivatives by thermal Claisen rearrangement.

Graphical abstractSeveral alkynyl epoxides and one alkynyl allyl alcohol were isomerized to cyclic allyl vinyl ethers using PtCl2 as the catalyst.Figure optionsDownload full-size imageDownload as PowerPoint slide