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Base-Promoted Stereoselective Hydrogenation of Ynamides with Sulfonyl Hydrazide to Give Z-Enamides

Zemin Zhao, Qingyu Tian, Yanhui Chen, Si Wen, Yuqing Zhang and Guolin Cheng*

*College of Materials Science and Engineering, Huaqiao University, Xiamen, Fujian 361021, China, Email: glchenghqu.edu.cn

Z. Zhao, Q. Tian, Y. Chen, S. Wen, Y. Zhang, G. Cheng, J. Org. Chem., 2021, 86, 10407-10413.

DOI: 10.1021/acs.joc.1c01085 (free Supporting Information)



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Abstract

A base-mediated semihydrogenation of ynamides using p-toluenesulfonyl hydrazide as an inexpensive and easy-to-handle hydrogen donor provides the thermodynamically unfavorable Z-enamides exclusively without overhydrogenation and reduction of other functional groups.


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proposed mechanism



Key Words

semihydrogenation, enamides, p-toluenesulfonyl hydrazide


ID: J42-Y2021