Palladium-catalyzed stereoselective (3+2) cycloaddition of vinylethylene carbonates with cyclic N-sulfonyl ketimines

被引：13

作者：

Gao, Xing ^{[1
,2
]}

Zhu, Dongyu ^{[1
,2
]}

Jiang, Feng ^{[1
,2
]}

Liao, Jianning ^{[1
,2
]}

Wang, Wei ^{[3
]}

Wu, Yongjun ^{[3
]}

Zheng, Lufei ^{[4
]}

Guo, Hongchao ^{[1
,2
,5
]}

机构：

[1] China Agr Univ, Dept Chem, Beijing 100193, Peoples R China

[2] China Agr Univ, Innovat Ctr Pesticide Res, Beijing 100193, Peoples R China

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

[4] Chinese Acad Agr Sci, Inst Qual Stand & Testing Technol Agroprod, Beijing 100081, Peoples R China

[5] China Agr Univ, Dept Nutr & Hlth, Beijing 100193, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2021年 / 19卷 / 22期

基金：

中国国家自然科学基金;

关键词：

DECARBOXYLATIVE CYCLOADDITION; ENANTIOSELECTIVE CONSTRUCTION; AZOMETHINE YLIDES; TERTIARY; ACCESS; FERMENTATION; HETEROCYCLES; SPIROKETALS; ALLYLATION; ANNULATION;

D O I：

10.1039/d1ob00614b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A diastereoselective (3 + 2) cycloaddition of N-sulfonyl ketimines with vinylethylene carbonates (VECs) in the presence of Pd(2)dba(3)center dot CHCl3 and PPh3 has been developed. The reaction of various substituted VECs and diverse cyclic N-sulfonyl ketimines proceeded smoothly under mild conditions, giving highly functionalized oxazolidine frameworks in good to excellent yields with moderate to good diastereoselectivities. With the use of spiroketal-based diphosphine SKP as a chiral ligand, an asymmetric version of the current (3 + 2) cycloaddition was achieved, and chiral products were obtained in >99% ee in most cases.

引用

页码：4877 / 4881

页数：5

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