Catalytic asymmetric ring-opening of meso-aziridines with malonates under heterodinuclear rare earth metal Schiff base catalysis.
Catalytic asymmetric ring-opening of meso-aziridines with malonates under heterodinuclear rare earth metal Schiff base catalysis.
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DOI：
10.1021/ja201492x
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发表时间：
2011-03
影响因子：
15
通讯作者：
Yingjie Xu;Luqing Lin;M. Kanai;S. Matsunaga;M. Shibasaki
中科院分区：
文献类型：
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作者：
Yingjie Xu;Luqing Lin;M. Kanai;S. Matsunaga;M. Shibasaki
研究了丙二酸酯催化meso-氮杂环丙烷的不对称开环反应。两种不同性质的稀土金属源的组合使用促进了所需的开环反应。La（O-iPr）（3）/Yb（OTf）（3）/Schiff碱1a（0.25-10 mol %）的1：1：1混合物有效地促进了五元环、六元环和七元环内消旋氮杂环丙烷以及无环内消旋氮杂环丙烷与丙二酸二甲酯、二乙酯和二苄基酯的反应，以99-63%的产率和>99.5-97% ee得到手性环状和无环γ-氨基酯。
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.