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

Hiroyuki Suga; Daisuke Ishimoto; Satoshi Higuchi; Motoo Ohtsuka; Tadashi Arikawa; Teruko Tsuchida; Akikazu Kakehi; Toshihide Baba

doi:10.1021/ol701936b

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

Org Lett. 2007 Oct 11;9(21):4359-62. doi: 10.1021/ol701936b. Epub 2007 Sep 20.

Authors

Hiroyuki Suga¹, Daisuke Ishimoto, Satoshi Higuchi, Motoo Ohtsuka, Tadashi Arikawa, Teruko Tsuchida, Akikazu Kakehi, Toshihide Baba

Affiliation

¹ Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University, Wakasato, Nagano 380-8553, Japan. sugahio@shinshu-u.ac.jp

PMID: 17880234
DOI: 10.1021/ol701936b

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.