Enantioselective 1,3-Dipolar (5+3) Cycloadditions of Oxidopyrylium Ylides and Vinylcyclopropanes toward 9-Oxabicyclononanes
Yanfeng Gao, Yuanhao Mao, Zhiwei Miao
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.
Topics & Concepts
StereocenterEnantioselective synthesisChemistryCycloadditionLigand (biochemistry)Combinatorial chemistryCatalysisStereochemistryOrganic chemistryReceptorBiochemistryCyclopropane Reaction MechanismsCatalytic Alkyne ReactionsOxidative Organic Chemistry Reactions