The dynamic kinetic resolution of azlactones with thiol nucleophiles catalyzed by arylated, deoxygenated cinchona alkaloids

The Journal of Organic Chemistry
Zaida Rodríguez-DocampoStephen J Connon

Abstract

A significant improvement of the available organocatalytic methods (in terms of product substrate scope and product enantiomeric excess) for the generation of enantioenriched α-amino acid thioesters via the dynamic kinetic resolution of azlactones is reported. C-9 arylated cinchona alkaloid catalysts have been found to be considerably superior to other bifunctional alkaloid catalysts as the promoters of this asymmetric process.

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Citations

Jan 7, 2014·The Journal of Physical Chemistry. a·Hai-Zhu YuGuo-Hua Hu
Jan 18, 2014·Organic Letters·Baokun QiaoZhiyong Jiang
Sep 23, 2014·Angewandte Chemie·Ryosuke TakedaVadim A Soloshonok
Aug 26, 2015·Chemical Communications : Chem Comm·Kunru YuXiaoming Feng
Jun 2, 2016·Chemistry : a European Journal·Pedro P de CastroGiovanni W Amarante
Aug 22, 2014·Chemical Reviews·Pankaj ChauhanDieter Enders
Apr 22, 2015·Organic & Biomolecular Chemistry·Shao-Yun ZhangXing-Wang Wang
Nov 23, 2017·Chemical Communications : Chem Comm·Zi-Song CongLin He
Aug 14, 2021·Organic & Biomolecular Chemistry·Sarah A Cronin, Stephen J Connon
Oct 30, 2020·Journal of the American Chemical Society·Ming-Sheng XieHai-Ming Guo
Sep 1, 2021·The Journal of Organic Chemistry·Pedro P De CastroHélio F Dos Santos

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