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Enantioselective 1,3-Dipolar (5+3) Cycloadditions of Oxidopyrylium Ylides and Vinylcyclopropanes toward 9-Oxabicyclononanes.

We have developed an efficient and mild enantioselective palladium-catalyzed (5+3) cycloaddition of vinylcyclopropanes and oxidopyrylium ylides generated in situ from benzopyranones, in the presence of a chiral PHOX ligand. These… Click to show full abstract

We have developed an efficient and mild enantioselective palladium-catalyzed (5+3) cycloaddition of vinylcyclopropanes and oxidopyrylium ylides generated in situ from benzopyranones, in the presence of a chiral PHOX ligand. These reactions afford various highly functionalized bridged oxa-[3.3.1]carbocycles with three stereogenic centers that are challenging to synthesize, in moderate to good yields and enantioselectivities.

Keywords: oxidopyrylium ylides; cycloadditions oxidopyrylium; enantioselective dipolar; vinylcyclopropanes toward; ylides vinylcyclopropanes; dipolar cycloadditions

Journal Title: Organic letters
Year Published: 2022

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