发布时间：

2025-11

影响因子：

14.7

DOI码：

10.1038/s41467-023-40409-4

论文名称：

Copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of 1,3-enynes and azomethine ylides

发表刊物：

NATURE COMMUNICATIONS

摘要：

Herein, we report a copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides and 1,3-enynes, which provides a series of chiral poly-substituted pyrrolidines in high regio-, diastereo-, and enantioselectivities. Both 4-aryl-1,3-enynes and 4-silyl-1,3-enynes serve as suitable dipolarophiles while 4-alkyl-1,3-enynes are inert. Moreover, the method is successfully applied in the construction of both tetrasubstituted stereogenic carbon centers and chiral spiro pyrrolidines. The DFT calculations are also conducted, which imply a concerted mechanism rather than a stepwise mechanism. Finally, various transformations started from the pyrrolidine bearing a triethylsilylethynyl group and centered on the alkyne group are achieved, which compensates for the inertness of 4-alkyl-1,3-enynes in the present reaction. One of the most efficient method to access chiral poly-substituted pyrrolidines is the catalytic asymmetric 1,3-dipolar cycloaddition, but using this reaction with weakly activated alkenes remains elusive. Here, the authors disclose a copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides and 1,3-enynes.

第一作者：

wangboran

论文类型：

期刊论文

通讯作者：

田平,liqinghua,殷亮

卷号：

14

期号：

1

ISSN号：

2041-1723

是否译文：

否

发表时间：

2023-08

他引次数：

12