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Catalytic Asymmetric Ring-Opening of meso-Aziridines with Malonates under Heterodinuclear Rare Earth Metal Schiff Base Catalysis

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posted on 20.04.2011, 00:00 by Yingjie Xu, Luqing Lin, Motomu Kanai, Shigeki Matsunaga, Masakatsu Shibasaki
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.