Organocatalytic enantio- and diastereoselective synthesis of 3,5-disubstituted prolines

被引：6

作者：

Riano, Iker ^{[1
]}

Diaz, Estibaliz ^{[1
]}

Uria, Uxue ^{[1
]}

Reyes, Efraim ^{[1
]}

Carrillo, Luisa ^{[1
]}

Vicario, Jose L. ^{[1
]}

机构：

[1] Univ Basque Country UPV EHU, Dept Organ Chem 2, POB 644, Bilbao 48080, Spain

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 11期

关键词：

ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; AZOMETHINE YLIDES; MICHAEL REACTIONS; AMINO-ACIDS; PYRROLIDINE; CATALYSIS; PIPERIDINE; CYCLOADDITION; DERIVATIVES;

D O I：

10.1039/c5cc09329e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The asymmetric synthesis of substituted pyrrolidines has been accomplished using a novel organocatalytic cyclization reaction promoted by a Cinchona alkaloid based primary amine. The reaction proceeds smoothly yielding pyrrolidine-2,2-dicarboxylates after in situ diastereoselective reduction with high levels of enantio-selection. Furthermore, these adducts could be easily transformed into N-protected disubstituted prolines through the base-promoted diastereoselective C -> N alkoxycarbonyl transfer reaction.

引用

页码：2330 / 2333

页数：4

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