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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

Author:
Mizota, Isao, Tadano, Yurie, Nakamura, Yusuke, Haramiishi, Tomoki, Hotta, Miyuki, Shimizu, Makoto
Source:
Organic letters 2019 v.21 no.8 pp. 2663-2667
ISSN:
1523-7052
Subject:
chemical reactions, chemical structure, nitrogen, piperidines, pyrrolidines, silica gel
Abstract:
Umpolung reactions of N-trimethylsilyl α-iminoester with organometallics gave directly N-alkylaminoesters in high yields without the need for removing a protecting group at the nitrogen atom. Efficient syntheses of pyrrolidines, piperidines, and iminodiacetate derivatives were also developed via tandem N,N- or N,C-dialkylation reactions utilizing characteristics of the silyl substituent. Furthermore, under the influence of silica gel, the addition of an enolate to the imino nitrogen proceeded to give an iminodiacetate derivative.
Agid:
6375937