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Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl α-Iminoesters through Auto-Tandem Catalysis

Azusa Kondoh, Masahiro Terada*

*Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan, Email: mteradam.tohoku.ac.jp

A. Kondoh, M. Terada, Org. Lett., 2018, 20, 5309-5313.

DOI: 10.1021/acs.orglett.8b02236 (free Supporting Information)


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Abstract

Auto-tandem catalysis with an organosuperbase as the catalyst enables a reductive cyclization of alkynyl α-iminoesters in the presence of 1-dodecanethiol as the reductant to provide N-H indoline derivatives under mild conditions via formation of α-aminoesters and an intramolecular addition of ester enolates to an alkyne.


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Key Words

indolines


ID: J54-Y2018