Torsak LuanphaisarnnontMahidol University2018-11-092018-11-092014-12-10Tetrahedron Letters. Vol.55, No.50 (2014), 6803-680718733581004040392-s2.0-84910678550https://repository.li.mahidol.ac.th/handle/20.500.14594/33201© 2014 Elsevier Ltd. All rights reserved. Catalytic asymmetric Diels-Alder reactions of N-allenoyloxazolidinones were investigated. Various chiral metal-bis(oxazoline) and metal-pyridinebis(oxazoline) complexes were screened. Cu(SbF6)2(H2O)2(t-BuBox) was found to be the most effective catalyst, giving the product in high yield, enantioselectivity, and endo:exo selectivity. The relative reactivity between N-allenoyloxazolidinones and N-alkenoyloxazolidinones was also investigated. A model for stereoinduction was proposed to account for the enantioselectivity and endo:exo selectivity.Mahidol UniversityBiochemistry, Genetics and Molecular BiologyChemistryPharmacology, Toxicology and PharmaceuticsArticleSCOPUS10.1016/j.tetlet.2014.10.051