Fungicide-inspired precursors of π-allylpalladium intermediates for palladium-catalyzed decarboxylative cycloadditions

被引：32

作者：

Li, Kuan ^{[1
]}

Zhen, Shuo ^{[1
]}

Wang, Wang ^{[1
]}

Du, Juan ^{[1
]}

Yu, Songcheng ^{[2
]}

Wu, Yongjun ^{[2
]}

Guo, Hongchao ^{[1
]}

机构：

[1] China Agr Univ, Innovat Ctr Pesticide Res, Dept Chem, Beijing 100193, Peoples R China

[2] Zhengzhou Univ, Coll Publ Hlth, Zhengzhou 450001, Peoples R China

来源：

CHEMICAL SCIENCE | 2023年 / 14卷 / 11期

基金：

中国国家自然科学基金;

关键词：

METHYLIDENE-DELTA-VALEROLACTONES; ASYMMETRIC 3+2 CYCLOADDITION; VINYLETHYLENE CARBONATES; ENANTIOSELECTIVE SYNTHESIS; CONSTRUCTION; REARRANGEMENT; ACCESS;

D O I：

10.1039/d3sc00112a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Inspired by a fungicide, we designed 5-vinyloxazolidine-2,4-diones as new precursors of pi-allylpalladium zwitterionic intermediates and developed palladium-catalyzed asymmetric (5 + 3) cycloaddition with azomethine imines and (3 + 2) cycloaddition with 1,1-dicyanoalkenes. Both reactions proceeded smoothly under mild reaction conditions to produce various chiral heterocyclic compounds in high yields with excellent enantioselectivities. These results revealed that 5-vinyloxazolidine-2,4-diones were a type of suitable precursor for palladium catalysis and will find extensive applications in Pd-catalyzed reactions such as cycloaddition and allylic alkylation.

引用

页码：3024 / 3029

页数：6

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