Lewis Acid-Catalyzed Diastereoselective Synthesis of Multisubstituted N-Acylaziridine-2-carboxamides from 2H-Azirines via Joullie-Ugi Three-Component Reaction

被引：23

作者：

Angyal, Aniko ^{[1
,2
]}

Demjen, Andras ^{[1
,2
]}

Weber, Edit ^{[3
]}

Kovacs, Anita K. ^{[4
]}

Wolfling, Janos ^{[2
]}

Puskas, Laszlo G. ^{[1
]}

Kanizsai, Ivan ^{[1
]}

机构：

[1] AVIDIN Ltd, Also Kikoto Sor 11-D, H-6726 Szeged, Hungary

[2] Univ Szeged, Dept Organ Chem, Dom Ter 8, H-6720 Szeged, Hungary

[3] Univ Szeged, Inst Pharmaceut Anal, SZTE MTA Lendulet Foldamer Res Grp, Somogyi U 4, H-6720 Szeged, Hungary

[4] Univ Szeged, Dept Med Chem, Dom Ter 8, H-6720 Szeged, Hungary

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 07期

关键词：

MULTICOMPONENT REACTIONS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; CYSTEINE PROTEASES; 3+2 CYCLOADDITION; PHASE SYNTHESIS; AZIRIDINE; SITE; PEPTIDES; FUNCTIONALIZATION;

D O I：

10.1021/acs.joc.7b03189

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A ZnCl2-catalyzed diastereoselective Joullie Ugi three-component reaction from 2H-azirines, isocyanides, and carboxylic acids was established. The protocol allows the preparation of highly and diversely functionalized N-acylaziridine-2-carboxamide derivatives in up to 82% isolated yields. Moreover, the applicability of N-acylaziridines is demonstrated through a variety of transformations.

引用

页码：3570 / 3581

页数：12

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