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Get Free AccessAbstract 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. magnified image
Banruo Huang, Ying He, Mark D. Levin, Jaime A. S. Coelho, Robert G. Bergman, Dean Toste (2019). Enantioselective Kinetic Resolution/Desymmetrization of <i>Para</i>‐Quinols: A Case Study in Boronic‐Acid‐Directed Phosphoric Acid Catalysis. , 362(2), DOI: https://doi.org/10.1002/adsc.201900816.
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Type
Article
Year
2019
Authors
6
Datasets
0
Total Files
0
Language
en
DOI
https://doi.org/10.1002/adsc.201900816
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