Catalytic Enantioselective Strecker Reaction of Isatin-Derived N-Unsubstituted Ketimines
Tetsuya Kadota, Masanao Sawa, Yuta Kondo, Hiroyuki Morimoto, Takashi Ohshima
Abstract
A catalytic enantioselective Strecker reaction of isatin-derived N-unsubstituted ketimines directly afforded the N-unprotected α-aminonitriles with a tetrasubstituted carbon stereocenter in up to 99% ee without requiring protection/deprotection steps. One-pot Strecker reactions from the parent carbonyl compounds were also realized with comparable yields and enantioselectivities. Direct transformations of the N-unprotected α-aminonitrile products streamlined the synthesis of unnatural amino acid derivatives and achieved the shortest one-pot stereoselective routes to a biologically active compound reported to date.
Topics & Concepts
Strecker amino acid synthesisStereocenterChemistryEnantioselective synthesisIsatinCatalysisOrganic chemistryStereoselectivityReaction conditionsAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisSynthesis and Catalytic Reactions