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Enantioselective Kinetic Resolution/Desymmetrization of Para-Quinols: A Case Study in Boronic-Acid-Directed Phosphoric Acid Catalysis.
- Author(s): Huang, Banruo;
- He, Ying;
- Levin, Mark D;
- Coelho, Jaime AS;
- Bergman, Robert G;
- Toste, F Dean
- et al.
Published Web Location
https://doi.org/10.1002/adsc.201900816Abstract
A chiral phosphoric acid-catalyzed kinetic resolution and desymmetrization of para-quinols operating via oxa-Michael addition was developed and subsequently subjected to mechanistic study. Good to excellent s-factors/enantioselectivities were obtained over a broad range of substrates. Kinetic studies were performed, and DFT studies favor a hydrogen bonding activation mode. The mechanistic studies provide insights to previously reported chiral anion phase transfer reactions involving chiral phosphate catalysts in combination with boronic acids.
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