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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
- Mizota, Isao, Tadano, Yurie, Nakamura, Yusuke, Haramiishi, Tomoki, Hotta, Miyuki, Shimizu, Makoto
- Organic letters 2019 v.21 no.8 pp. 2663-2667
- chemical reactions, chemical structure, nitrogen, piperidines, pyrrolidines, silica gel
- 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.