立体中心
环加成
烷基
化学
吡咯烷
催化作用
炔烃
芳基
甲亚胺叶立德
组合化学
化学选择性
1,3-偶极环加成
立体化学
药物化学
对映选择合成
有机化学
作者
Boran Wang,Yanbo Li,Qi Zhang,Dingding Gao,Ping Tian,Qinghua Li,Liang Yin
标识
DOI:10.1038/s41467-023-40409-4
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.
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