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Tandem N,N-Dialkylation Reaction of N-Trimethylsilyl α-Iminoesters Utilizing an Umpolung Reaction and Characteristics of the Silyl Substituent: Synthesis of Pyrrolidine, Piperidine, and Iminodiacetate

Isao Mizota, Yurie Tadano, Yusuke Nakamura, Tomoki Haramiishi, Miyuki Hotta, Makoto Shimizu*

*Department of Chemistry for Materials, Graduate School of Engineering, Mie University, Tsu, Mie 514-8507, Japan, Email:

I. Mizota, Y. Tadano, Y. Nakamura, T. Haramiishi, M. Hotta, M. Shimizu, Org. Lett., 2019, 21, 2663-2667.

DOI: 10.1021/acs.orglett.9b00654


Umpolung reactions of N-trimethylsilyl α-iminoester with organometallics provide deprotected N-alkylaminoesters. Furthermore, tandem N,N- or N,C-dialkylation reactions enable efficient syntheses of pyrrolidines, piperidines, and iminodiacetate derivatives.

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Key Words

α-amino acids, secondary amines

ID: J54-Y2019