Catalytic Enantioselective Strecker Reaction of Isatin-Derived N-Unsubstituted Ketimines

Tetsuya Kadota, Masanao Sawa, Yuta Kondo, Hiroyuki Morimoto, Takashi Ohshima

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)4553-4558
Number of pages6
JournalOrganic letters
Volume23
Issue number12
DOIs
Publication statusPublished - Jun 18 2021

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