Organic Chemistry Portal

Abstracts

Search:

Copper-Catalyzed Asymmetric Oxidative Desymmetrization of 2-Substituted 1,2,3-Triols

Kosuke Yamamoto, Yu Suganomata, Takumi Inoue, Masami Kuriyama, Yosuke Demizu and Osamu Onomura*

*Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan, Email: onomuranagasaki-u.ac.jp

K. Yamamoto, Y. Suganomata, T. Inoue, M. Kuriyama, Y. Demizu, O. Onomura, J. Org. Chem., 2022, 87, 6479-6491.

DOI: 10.1021/acs.joc.2c00398



see article for more reactions

Abstract

A chiral bisoxazoline ligand/copper catalyst system mediates an asymmetric oxidative desymmetrization of readily accessible 2-(hetero)aryl- and alkyl-substituted glycerols with 1,3-dibromo-5,5-dimethylhydantoin and MeOH. The present transformation provides straightforward access toward various glycerate derivatives in good yields with high enantioselectivities.

see article for more examples



Key Words

oxidation of alcohols, DBDMH


ID: J42-Y2022