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Synthesis of Chiral Esters via Asymmetric Wolff Rearrangement Reaction

Jing Meng, Wei-Wei Ding and Zhi-Yong Han*

*Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, China, Email: hanzy2014ustc.edu.cn

J. Meng, W.-W. Ding, Z.-Y. Han, Org. Lett., 2019, 21, 9801-9805.

DOI: 10.1021/acs.orglett.9b03227 (free Supporting Information)


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Abstract

An asymmetric Wolff rearrangement reaction directly converts α-diazoketones into broadly useful chiral α,α-disubstituted carboxylic esters with high enantioselectivities using visible-light-induced formation of the ketene intermediate and a readily available benzotetramisole-type catalyst for the asymmetric ketene esterification.

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Key Words

Wolff rearrangement, organocatalysis, photochemistry


ID: J54-Y2019