AI Article Synopsis
- Allenic amides act as effective dipolarophiles in reactions with vinyl epoxides through Pd-catalysis.
- The chiral NHC ligand plays a crucial role in achieving asymmetry in the [3 + 2] cycloaddition process.
- This method produces chiral tetrahydrofurans that contain multiple functional groups and various stereocenters with high yields and selectivity.
Article Abstract
Allenic amides are successfully developed as dipolarophiles to react with vinyl epoxides under Pd-catalysis. The chiral NHC showed its unique role as the ligand in this asymmetric [3 + 2] cycloaddition. Chiral tetrahydrofurans bearing three functional groups (monosubstituted alkene, tetrasubstituted enolether, and amide) and vicinal tertiary and quaternary stereocenters were obtained in high yields with high diastereo- and enantioselectivities.
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| http://dx.doi.org/10.1021/acs.orglett.8b01886 | DOI Listing |
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