Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 15, Pages 5791-5793Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja201492x
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Funding
- JSPS
- Takeda Science foundation
- Inoue Science Foundation
- Uehera Memorial Foundation
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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 la (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 gamma-amino esters in 99-63% yield and > 99.5-97% ee.
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