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2005•Advanced Synthesis & CatalysisOpen access

Transfer Hydrogenation of α‐Branched Ketimines: Enantioselective Synthesis of Cycloalkylamines via Dynamic Kinetic Resolution

Abel Ros, Antonio Magriz, Hansjörg Dietrich, Mark James Ford, Rosario Fernández, José M. Lassaletta

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Abstract

Abstract The transfer hydrogenation of 2‐substituted bicyclic and monocyclic ketimines using HCO2H/ Et3N as the hydrogen source and TsDPEN‐based Ru(II) and Ir(III) catalysts proceeds with dynamic kinetic resolution to afford the corresponding cis‐cycloalkylamines with moderate to excellent levels of diastero‐ and enantioselectivity. A “one‐pot” procedure starting from ketones as starting materials with in situ formation of the reacting imines has also been developed.

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Abstract The transfer hydrogenation of 2‐substituted bicyclic and monocyclic ketimines using HCO2H/ Et3N as the hydrogen source and TsDPEN‐based Ru(II) and Ir(III) catalysts proceeds with dynamic kinetic resolution to afford the corresponding cis‐cycloalkylamines with moderate to excellent levels of diastero‐ and enantioselectivity. A “one‐pot” procedure starting from ketones as starting materials with in situ formation of the reacting imines has also been developed.

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Available abstract

Abstract The transfer hydrogenation of 2‐substituted bicyclic and monocyclic ketimines using HCO2H/ Et3N as the hydrogen source and TsDPEN‐based Ru(II) and Ir(III) catalysts proceeds with dynamic kinetic resolution to afford the corresponding cis‐cycloalkylamines with moderate to excellent levels of diastero‐ and enantioselectivity. A “one‐pot” procedure starting from ketones as starting materials with in situ formation of the reacting imines has also been developed.

Key concepts: Chemistry, Kinetic resolution, Enantioselective synthesis, Transfer hydrogenation, Bicyclic molecule, Catalysis, Kinetic energy, Organic chemistry

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