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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 A. S.,
Bergman Robert G.,
Toste F. Dean
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900816
Subject(s) - desymmetrization , chemistry , kinetic resolution , phosphoric acid , enantioselective synthesis , boronic acid , catalysis , organic chemistry , combinatorial chemistry , organocatalysis , stereochemistry
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.