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: mshimizu
chem.mie-u.ac.jp
I. Mizota, Y. Tadano, Y. Nakamura, T. Haramiishi, M. Hotta, M. Shimizu, Org. Lett., 2019, 21, 2663-2667.
DOI: 10.1021/acs.orglett.9b00654
Abstract
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
