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
收藏
页码：4877 / 4881
页数：5
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