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

Bo-Ran Wang, Yan-Bo Li, Qi Zhang, Dingding Gao, Ping Tian (), Qinghua Li () and Liang Yin ()
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Bo-Ran Wang: Shanghai University of Traditional Chinese Medicine
Yan-Bo Li: University of Chinese Academy of Sciences, Chinese Academy of Sciences
Qi Zhang: University of Chinese Academy of Sciences, Chinese Academy of Sciences
Dingding Gao: Shanghai University of Traditional Chinese Medicine
Ping Tian: Shanghai University of Traditional Chinese Medicine
Qinghua Li: Shanghai University of Traditional Chinese Medicine
Liang Yin: Shanghai University of Traditional Chinese Medicine

Nature Communications, 2023, vol. 14, issue 1, 1-11

Abstract: Abstract 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.

Date: 2023
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DOI: 10.1038/s41467-023-40409-4

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