Copper-Catalyzed [2,3]-Sigmatropic Rearrangement of Azide-Ynamides via Selenium Ylides

Chong-Yang Shi; Xuan Wang; Xin Liu; Zu-Hui Ai; Shuai Xiong; Long-Wu Ye; Bo Zhou; Xin-Qi Zhu

doi:10.1021/acs.orglett.4c04444

Copper-Catalyzed [2,3]-Sigmatropic Rearrangement of Azide-Ynamides via Selenium Ylides

Org Lett. 2024 Dec 23. doi: 10.1021/acs.orglett.4c04444. Online ahead of print.

Authors

Chong-Yang Shi¹, Xuan Wang², Xin Liu², Zu-Hui Ai¹, Shuai Xiong¹, Long-Wu Ye^{1

2

3}, Bo Zhou², Xin-Qi Zhu¹

Affiliations

¹ Yunnan Key Laboratory of Modern Separation Analysis and Substance Transformation, College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, China.
² Key Laboratory for Chemical Biology of Fujian Province and State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.
³ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.

PMID: 39714429
DOI: 10.1021/acs.orglett.4c04444

Abstract

A copper-catalyzed [2,3]-sigmatropic rearrangement of azide-ynamides via selenium ylides is disclosed, which leads to the practical and divergent synthesis of a variety of tricyclic heterocycles bearing a quaternary carbon stereocenter in generally moderate to excellent yields. Significantly, this method represents the first [2,3]-sigmatropic rearrangement of the selenium ylide based on alkynes and an unprecedented [2,3]-sigmatropic rearrangement via α-imino copper carbenes.