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Asymmetric Umpolung Hydrogenation and Deuteration of Alkenes Catalyzed by Nickel

Siyu Guo, Xiuhua Wang and Jianrong Steve Zhou*

*Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371 Singapore, Email: jrzhountu.edu.sg

S. Guo, X. Wang, J. S. Zhou, Org. Lett., 2020, 22, 1204-1207.

DOI: 10.1021/acs.orglett.0c00112


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Abstract

Nickel-catalyzed asymmetric hydrogenation of α,β-unsaturated esters, nitriles, and ketones as well as allylic alcohols proceeds in high enantioselectivity, using acetic acid or water as the hydrogen source and indium powder as electron donor. Asymmetric deuteration of α,β-unsaturated esters is achieved with the use of deuterated water.

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N,N-Dimethylformamide as Hydride Source in Nickel-Catalyzed Asymmetric Hydrogenation of α,β-Unsaturated Esters

S. Guo, J. Zhou, Org. Lett., 2016, 18, 5344-5347.


Key Words

reduction of α,β-unsaturated compounds, indium


ID: J54-Y2020