银催化的亚胺叶立德与β-硼基丙烯酰胺的 1,3-偶极环加成反应。

Silver-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with β-boryl acrylates.

机构信息

Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain.

出版信息

J Org Chem. 2011 Mar 18;76(6):1945-8. doi: 10.1021/jo1024915. Epub 2011 Feb 21.

DOI:10.1021/jo1024915

PMID:21332240

Abstract

The Ag-catalyzed 1,3-dipolar cycloaddition of (Ε)-β-borylacrylates with azomethine ylides is described. The resulting 3-borylpyrrolidine derivatives were obtained in high yields and complete endo selectivities using AgOAc/dppe as catalyst system and B(dam) as boryl group. Transformation of the B(dam) group into pinacol borane and oxidation afforded 3-hydroxyproline derivatives in high yields.

摘要

Ag 催化的（E）-β-硼酸丙烯酰胺与亚胺叶立德的 1,3-偶极环加成反应被描述。使用 AgOAc/dppe 作为催化剂体系和 B(dam) 作为硼基团，得到了高产率和完全内选择性的 3-硼基吡咯烷衍生物。B(dam) 基团转化为频哪醇硼烷和氧化，高产率得到 3-羟基脯氨酸衍生物。