Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, USA.
J Org Chem. 2010 Dec 3;75(23):8271-4. doi: 10.1021/jo101304q. Epub 2010 Oct 29.
Building on the observation that metal complexation facilitates azomethine ylide formation, we report that chelating aldehydes participate in metal-templated, one-pot reactions with unprotected amino acid esters and activated olefins to provide highly substituted pyrrolidines. The high yields, broad substrate scope, excellent diastereoselectivities, functional group tolerance, and incorporation of commercially available materials in this reaction simplifies access to medicinally relevant proline derivatives.
基于金属络合促进亚胺叶立德形成的观察结果，我们报告说，螯合醛与未保护的氨基酸酯和活化烯烃参与金属模板的一锅反应，提供高取代的吡咯烷。该反应具有高产率、广泛的底物范围、优异的非对映选择性、官能团耐受性以及可商购材料的应用，简化了具有药用相关性脯氨酸衍生物的获得途径。
