Dipole-LUMO/dipolarophile-HOMO controlled asymmetric cycloadditions of carbonyl ylides catalyzed by chiral Lewis acids.

Abstract

We have found the first successful example of reverse-electron-demand dipole-LUMO/dipolarophile-HOMO controlled cycloaddition reactions between carbonyl ylides, which were generated from o-methoxycarbonyl-alpha-diazoacetophenone and their acyl derivatives as precursors, and vinyl ether derivatives with high levels of asymmetric induction (97-77% ee) using chiral 2,6-(oxazolinyl)pyridine-Eu(III) or binaphthyldiimine-Ni(II) complexes as chiral Lewis acid catalysts.

Cite this paper

@article{Suga2007DipoleLUMOdipolarophileHOMOCA, title={Dipole-LUMO/dipolarophile-HOMO controlled asymmetric cycloadditions of carbonyl ylides catalyzed by chiral Lewis acids.}, author={Hiroyuki Suga and Daisuke Ishimoto and Satoshi Higuchi and Motoo Ohtsuka and Tadashi Arikawa and Teruko Tsuchida and Akikazu Kakehi and Toshihide Baba}, journal={Organic letters}, year={2007}, volume={9 21}, pages={4359-62} }