Organocatalytic Direct Enantioselective Hydrophosphonylation of <i>N</i> -Unsubstituted Ketimines for the Synthesis of α-Aminophosphonates
Koki Yamada, Yuta Kondo, Akihiko Kitamura, Tetsuya Kadota, Hiroyuki Morimoto, Takashi Ohshima
Abstract
We report an organocatalyzed direct enantioselective hydrophosphonylation of N -unsubstituted ketimines that affords N -unprotected α-tetrasubstituted α-aminophosphonates without protection/deprotection steps. The reaction is suitable for N -unsubstituted isatin-derived and trifluoromethyl ketimines, affording products in high yields with excellent enantioselectivity. Applications of the reaction and a proposed transition state model are also described.
Topics & Concepts
Enantioselective synthesisChemistryCatalysisIsatinOrganocatalysisTrifluoromethylOrganic chemistryCombinatorial chemistryAlkylOrganophosphorus compounds synthesisAsymmetric Hydrogenation and CatalysisFluorine in Organic Chemistry