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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: websterntu.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 (free Supporting Information)


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

β-hydroxy esters


ID: J48-Y2015