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Gold-Catalyzed Divergent N/O-Vinylations of trans-2-Butene-1,4-amino Alcohols with Alkynes and the Cascade Rearrangements/Cyclizations to Dihydropyrroles and Dihydrofurans

Xiao-Qian Zhang, Congdi Zhang, Zhiyou Hu and Youliang Wang*

*School of Chemistry, Xi'an Jiaotong University (XJTU), Xi'an 710049, China, Email: youliangwangxjtu.edu.cn

X.-Q. Zhang, C. Zhang, Z. Hu, Y. Wang, Org. Lett., 2023, 25, 5800-5805.

DOI: 10.1021/acs.orglett.3c02052


 

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Abstract

Gold-catalyzed divergent additions of trans-2-butene-1,4-amino alcohols to alkynes provide functionalized dihydropyrrole and dihydrofuran products via a cascade (Aza-) Claisen rearrangement/cyclization sequence of the intermediate  allyl enamine and allyl vinyl ether adducts.

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Key Words

2-pyrrolines, 2,3-dihydrofurans


ID: J54-Y2023