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

被引：24

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

共 67 条

[1] A NOVEL SYNTHESIS OF BETA-LACTAMS [J].

ALPER, H ;

PERERA, CP ;

AHMED, FR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (05) :1289-1291

[2] Organocatalyzed nucleophilic addition of pyrazoles to 2H-azirines: asymmetric synthesis of 3,3-disubstituted aziridines and kinetic resolution of racemic 2H-azirines [J].

An, Dong ;

Guan, Xukai ;

Guan, Rui ;

Jin, Lajiao ;

Zhang, Guangliang ;

Zhang, Suoqin .

CHEMICAL COMMUNICATIONS, 2016, 52 (75) :11211-11214

[3] A new highly convergent entry to densely functionalized aziridines based on the Ugi reaction [J].

Banfi, Luca ;

Basso, Andrea ;

Guanti, Giuseppe ;

Paravidino, Monica ;

Riva, Renata .

QSAR & COMBINATORIAL SCIENCE, 2006, 25 (5-6) :457-460

[4] Long-range diastereoselectivity in Ugi reactions of 2-substituted dihydrobenzoxazepines [J].

Banfi, Luca ;

Basso, Andrea ;

Cerulli, Valentina ;

Rocca, Valeria ;

Riva, Renata .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 :976-979

[5] Asymmetric synthesis of β2-amino acids:: 2-substituted-3-aminopropanoic acids from N-acryloyl SuperQuat derivatives [J].

Beddow, James E. ;

Davies, Stephen G. ;

Ling, Kenneth B. ;

Roberts, Paul M. ;

Russell, Angela J. ;

Smith, Andrew D. ;

Thomson, James E. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (17) :2812-2825

[6] MODEL STUDIES DIRECTED TOWARD THE TOTAL SYNTHESIS OF 14-MEMBERED CYCLOPEPTIDE ALKALOIDS - SYNTHESIS OF PROLYL PEPTIDES VIA A 4-COMPONENT CONDENSATION [J].

BOWERS, MM ;

CARROLL, P ;

JOULLIE, MM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (05) :857-865

[7] Microwave-assisted ring expansion of N-acetyl 3′-unsubstituted aziridine in the presence of Lewis acids [J].

Cardillo, G ;

Gentilucci, L ;

Gianotti, M ;

Tolomelli, A .

TETRAHEDRON, 2001, 57 (14) :2807-2812

[8]

Cardillo G, 2001, EUR J ORG CHEM, V2001, P3545

[9] Diversity oriented and chemoenzymatic synthesis of densely functionalized pyrrolidines through a highly diastereoselective Ugi multicomponent reaction [J].

Cerulli, Valentina ;

Banfi, Luca ;

Basso, Andrea ;

Rocca, Valeria ;

Riva, Renata .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (06) :1255-1274

[10] Chiral Bronsted acid-catalyzed diastereo- and enantioselective synthesis of CF3-substituted aziridines [J].

Chai, Zhuo ;

Bouillon, Jean-Philippe ;

Cahard, Dominique .

CHEMICAL COMMUNICATIONS, 2012, 48 (76) :9471-9473

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