Diastereo- and Enantioselective Three-Component Coupling Approach to Highly Substituted Pyrrolidines

被引：22

作者：

Chaulagain, Mani Raj ^{[1
]}

Felten, Albert E. ^{[1
]}

Gilbert, Kevin ^{[1
]}

Aron, Zachary D. ^{[1
]}

机构：

[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 18期

关键词：

1,3-DIPOLAR CYCLOADDITION REACTIONS; AZOMETHINE YLIDES; INTRAMOLECULAR HYDROAMINATION; ASYMMETRIC-SYNTHESIS; ALKENES; DERIVATIVES; AZIRIDINES; COMPLEXES; POLYMERASE; INHIBITORS;

D O I：

10.1021/jo401015y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective synthesis of substituted pyrrolidines through a mild Lewis-acid catalyzed three-component coupling reaction between picolinaldehyde, amino acids, and activated olefins is reported. The reaction uses low catalyst loadings of commercially available chiral diamines and copper triflate proposed to self-assemble in conjunction with the chelating aldehydes, 4-substituted-2-picolinaldehydes or 4-methylthiazole-2-carboxaldehyde, to generate a catalyst complex. A model is provided to explain how this complex directs enantioselectivity. This work represents a significant advance in the ease, scope, and cost of producing highly substituted, enantioenriched pyrrolidines.

引用

页码：9471 / 9476

页数：6

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