Catalytic Hydrogenation of α,β-Epoxy Ketones to Form β-Hydroxy Ketones Mediated by an NADH Coenzyme Model
Hua-Jian Xu, You-Cheng Liu,* Yao Fu and Yun-Dong Wu
*Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China, College of Chemistry, Lanzhou University, Lanzhou, 730000, China, Email: ycliuustc.edu.cn
H.-J. Xu, Y.-C. Liu, Y. Fu, Y.-D. Wu, Org. Lett., 2006, 8, 3449-3451.
DOI: 10.1021/ol0610892 (free Supporting Information)
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The hydrogenation of α,β-epoxy ketones can be mediated by a catalytic amount of BNA+Br- using Na2S2O4 as primary reducing agent to form the corresponding β-hydroxy ketones in high yield. A radical mechanism has been proposed.
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H.-J. Xu, X. Wan, Y.-Y. Shen, S. Xu, Y.-S. Feng, Org. Lett., 2012, 14, 1210-1213.