Diastereoselectivity in Passerini Reactions of Chiral Aldehydes and in Ugi Reactions of Chiral Cyclic Imines

被引：19

作者：

Lambruschini, Chiara ^{[1
]}

Moni, Lisa ^{[1
]}

Banfi, Luca ^{[1
]}

机构：

[1] Univ Genoa, Dept Chem & Ind Chem, Via Dodecaneso 31, Genoa, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 25期

关键词：

Multicomponent reactions; Diastereoselectivity; Aldehydes; Isocyanides; Passerini reaction; STEREOSELECTIVE-SYNTHESIS; ALPHA-AMINOALDEHYDES; ASYMMETRIC-SYNTHESIS; PROLYL PEPTIDES; MULTICOMPONENT; PEPTIDOMIMETICS; CONDENSATION; PYRROLIDINES; HETEROCYCLES; DERIVATIVES;

D O I：

10.1002/ejoc.202000016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereoselectivity in Passerini and Ugi reactions of chiral aldehydes/imines remains challenging. Moreover, the Ugi reaction of chiral acyclic imines is complicated by their easy racemization/epimerization, whereas this problem is nearly completely suppressed using chiral cyclic imines in a modification called Ugi-Joullie reaction. Thus 3-component modification also allows a better diastereoselectivity thanks to the higher steric rigidity of rings. This review presents an overview of the current knowledge on diastereoselective Passerini reaction of chiral aldehydes, and on diastereoselective Ugi-Joullie reaction of chiral cyclic imines, focusing on the results gathered by the authors' research group.

引用

页码：3766 / 3778

页数：13

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