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Updated: Nov 4, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Catalytic Enantioselective Strecker Reaction of Isatin-Derived N-Unsubstituted Ketimines
Tetsuya Kadota1, Masanao Sawa1, Yuta Kondo1
1Graduate School of Pharmaceutical Sciences, Kyushu University, Maidashi 3-1-1 Higashi-ku, Fukuoka 812-8582, Japan.
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.
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