N-Heterocyclic Carbene-Catalyzed Radical Reactions for Highly Enantioselective β-Hydroxylation of Enals
Yuexia Zhang, Yu Du, Zhijian Huang, Jianfeng Xu, Xingxing Wu, Yuhuang Wang, Ming Wang, Song Yang, Richard D. Webster* and Yonggui Robin Chi*
*Division of Chemistry & Biological Chemistry, School of
Physical & Mathematical Sciences, Nanyang Technological University, Singapore
637371, Singapore, Email:
webster
ntu.edu.sg, robinchintu.edu.sg
Y. Zhang, Y. Du, Z. Huang, J. Xu, X. Wu, Y. Wang, M. Wang, S. Yang, R. D. Webster, Y. R. Chi, J. Am. Chem. Soc., 2015, 137, 2416-2419.
DOI: 10.1021/ja511371a
Abstract
An N-heterocyclic carbene-catalyzed oxidative single-electron-transfer reaction enables the β-hydroxylation of enals through a pathway involving multiple radical intermediates, as supported by experimental observations. The reaction allows a highly enantioselective access to β-hydroxyl esters that are widely found in natural products and bioactive molecules.
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Key Words
ID: J48-Y2015
