Organic Letters p. 2663 - 2667 (2019)
Update date:2022-08-02
Topics:
Mizota, Isao
Tadano, Yurie
Nakamura, Yusuke
Haramiishi, Tomoki
Hotta, Miyuki
Shimizu, Makoto
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.
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