A new highly convergent entry to densely functionalized aziridines based on the Ugi reaction

被引：12

作者：

Banfi, Luca ^{[1
]}

Basso, Andrea ^{[1
]}

Guanti, Giuseppe ^{[1
]}

Paravidino, Monica ^{[1
]}

Riva, Renata ^{[1
]}

机构：

[1] Dipartimento Chim & Chim Ind, I-16146 Genoa, Italy

来源：

QSAR & COMBINATORIAL SCIENCE | 2006年 / 25卷 / 5-6期

关键词：

multicomponent reactions; Ugi four-component reaction (U-4CR); isocyanide; aziridines; post-condensation transformations;

D O I：

10.1002/qsar.200540192

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The products of an Ugi-4CR employing lactate-derived O-protected alpha-hydroxycarbonyl derivatives underwent, during the subsequent O-deprotection reaction, an unexpected acyl migration from nitrogen to oxygen. After ester saponification, treatment of the resulting alpha-aminoalcohol with mesyl chloride gave rise to a regioselective and stereospecific cyclization to give a series of highly functionalized aziridines in good overall yield.

引用

页码：457 / 460

页数：4

共 20 条

[1]

ANTHOINEDIETRIC.S, 2005, ORG BIOMOL CHEM, V3, P97

[2] Enantio- and diastereoselective synthesis of 2,5-disubstituted pyrrolidines through a multicomponent Ugi reaction and their transformation into bicyclic scaffolds [J].