Enantioselective Kinetic Resolution/Desymmetrization of Para‐Quinols: A Case Study in Boronic‐Acid‐Directed Phosphoric Acid Catalysis. Issue 2 (24th September 2019)

• Record Type: Journal Article
• Authors: Huang, Banruo; He, Ying; Levin, Mark D.; Coelho, Jaime A. S.; Bergman, Robert G.; Toste, F. Dean
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 2(2020)
• Page Start: 295
• Page End: 301
• Publication Date: 2019-09-24
• Subjects: asymmetric catalysis -- chiral phosphoric acid -- reaction mechanisms -- kinetics -- directed reactivity -- oxa-Michael addition; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201900816
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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. Abstract :