Hydrogen-Bonding Assisted Catalytic Kinetic Resolution of Acyclic β-Hydroxy Amides
Arka Porey
School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata, 700032 India
Search for more papers by this authorBhaskar Deb Mondal
School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata, 700032 India
Search for more papers by this authorCorresponding Author
Dr. Joyram Guin
School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata, 700032 India
Search for more papers by this authorArka Porey
School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata, 700032 India
Search for more papers by this authorBhaskar Deb Mondal
School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata, 700032 India
Search for more papers by this authorCorresponding Author
Dr. Joyram Guin
School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata, 700032 India
Search for more papers by this authorGraphical Abstract
A method for catalytic kinetic resolution (KR) of acyclic α-substituted β-hydroxy amides was developed via enantioselective acylation of primary alcohol with an N-heterocyclic carbene. Enhanced selectivity was realized for the catalytic KR process using cyclic tertiary amine as a base additive. Diastereomeric transition state models are proposed to rationalize the origin of enantioselectivity.
Abstract
Enantioenriched acyclic α-substituted β-hydroxy amides are valuable compounds in chemical, material and medicinal sciences, but their enantioselective synthesis remains challenging. A catalytic kinetic resolution (KR) of such amides with selectivity factor(s) up to >200 is developed via enantioselective acylation of primary alcohol with N-heterocyclic carbene. An enhanced selectivity for the catalytic KR process is realized using cyclic tertiary amine as base additive. Diastereomeric transition state models for the process are proposed to rationalize the origin of enantioselectivity.
Supporting Information
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