Catalytic Asymmetric Ring-Opening of <i>meso-</i>Aziridines with Malonates under Heterodinuclear Rare Earth Metal Schiff Base Catalysis
Journal of the American Chemical SocietyPublished 28 March 2011
Yingjie Xu, Luqing Lin, Motomu Kanai, Shigeki Matsunaga, Masakatsu Shibasaki
Citations107
SJR quartileQ1
SJR score5.55
SNIP2.61
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TL;DR
The combined use of two rare earth metal sources with different properties promoted the desired ring-opening reaction and resulted in chiral cyclic and acyclic γ-amino esters in 99-63% yield and >99.5-97% ee.
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.
Keywords
ChemistryBiochemistry, Genetics and Molecular Biology
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