Palladium-Catalyzed Carbonylative [5+1] Cycloaddition of N-Tosyl Vinylaziridines: Solvent-Controlled Divergent Synthesis of α,β- and β,γ-Unsaturated δ-Lactams

被引：7

作者：

Zhang, Tao ^{[1
]}

Wang, Shichong ^{[2
]}

Zuo, Dandan ^{[3
]}

Zhao, Jingjing ^{[2
]}

Luo, Wen ^{[3
]}

Wang, Chaojie ^{[3
]}

Li, Pan ^{[1
]}

机构：

[1] Henan Univ, Coll Chem & Chem Engn, Key Lab Nat Med & Immuno Engn, Kaifeng 475004, Peoples R China

[2] Henan Univ, Coll Chem & Chem Engn, Kaifeng 475004, Peoples R China

[3] Henan Univ, Key Lab Nat Med & Immuno Engn, Kaifeng 475004, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 15期

基金：

中国博士后科学基金;

关键词：

RING-OPENING CYCLIZATION; VINYL AZIRIDINES; DECARBOXYLATIVE CARBONYLATION; FUNCTIONALIZED PYRROLIDINES; STEREOSPECIFIC SYNTHESIS; NITROGEN-HETEROCYCLES; IMINES; ACCESS; 3,6-DIHYDRO-1H-PYRIDIN-2-ONES; ANNULATION;

D O I：

10.1021/acs.joc.2c00710

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed carbonylative [5+1] cycloaddition of N-tosyl vinylaziridines with CO has been developed. This protocol affords an efficient and practical approach for solvent-controlled divergent synthesis of alpha,beta-unsaturated delta-lactams in dimethylformamide and beta,gamma-unsaturated delta-lactams in tetrahydrofuran in good to excellent yields. Significantly, the step- and atom-economical reactions are more regioselective toward [5+1] cycloaddition than toward [3+1] cydoaddition.

引用

页码：10408 / 10415

页数：8

共 48 条

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