Catalytic asymmetric ring-opening of meso-aziridines with malonates under heterodinuclear rare earth metal Schiff base catalysis

J Am Chem Soc. 2011 Apr 20;133(15):5791-3. doi: 10.1021/ja201492x. Epub 2011 Mar 28.

Abstract

Catalytic asymmetric ring-opening of meso-aziridines with malonates is described. The combined use of two rare earth metal sources with different properties promoted the desired ring-opening reaction. A 1:1:1 mixture of a heterobimetallic La(O-iPr)(3)/Yb(OTf)(3)/Schiff base 1a (0.25-10 mol %) efficiently promoted the reaction of five-, six-, and seven-membered ring cyclic meso-aziridines as well as acyclic meso-aziridines with dimethyl, diethyl, and dibenzyl malonates, giving chiral cyclic and acyclic γ-amino esters in 99-63% yield and >99.5-97% ee.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aziridines / chemistry*
  • Catalysis
  • Malonates / chemistry*
  • Metals, Rare Earth / chemistry*
  • Schiff Bases / chemistry*

Substances

  • Aziridines
  • Malonates
  • Metals, Rare Earth
  • Schiff Bases