通过催化不对称 1,3-偶极环加成反应，涉及 α-芳基甘氨酸酯，实现具有季立体中心的 2,5-二氢吡咯骨架的对映选择性构建。
Enantioselective construction of 2,5-dihydropyrrole skeleton with quaternary stereogenic center via catalytic asymmetric 1,3-dipolar cycloaddition involving α-arylglycine esters.
机构信息
School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, China.
出版信息
Org Biomol Chem. 2013 Mar 7;11(9):1482-9. doi: 10.1039/c2ob26566d.
A catalytic asymmetric construction of synthetically and biologically important 2,5-dihydropyrrole scaffolds with concomitant creation of multiple chiral carbon centers including one quaternary stereogenic center in high yields (up to 99%) and excellent enantioselectivities (up to 99% ee) has been established via an organocatalytic 1,3-dipolar cycloaddition using α-arylglycine esters as azomethine precursors. Moreover, a detailed investigation has been performed on the catalytic asymmetric 1,3-dipolar cycloadditions of α-arylglycine ester-generated azomethine ylides with alkynes, providing an efficient way to simultaneously access both 2,5-dihydropyrrole diastereomers in good enantioselectivities.
通过使用α-芳基甘氨酸酯作为亚胺前体的有机催化 1,3-偶极环加成反应，建立了一种催化不对称的构建具有合成和生物重要性的 2,5-二氢吡咯骨架的方法，同时在高收率（高达 99%）和优异的对映选择性（高达 99%ee）条件下，生成多个手性碳原子中心，包括一个季碳手性中心。此外，还对α-芳基甘氨酸酯生成的亚胺叶立德与炔烃的催化不对称 1,3-偶极环加成反应进行了详细的研究，为同时以良好的对映选择性获得两种 2,5-二氢吡咯非对映异构体提供了一种有效的方法。
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