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

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Abstract

A novel reductive cyclization of alkynyl α-iminoesters was developed through auto-tandem catalysis with a Brønsted base as the catalyst. The reaction system involves two mechanistically different elementary processes, both of which are efficiently catalyzed by an organosuperbase P2-tBu: the unprecedented reduction of α-iminoesters with 1-dodecanethiol as the reductant to provide α-aminoesters and the following intramolecular addition of ester enolates to an alkyne. The operationally simple reaction under mild conditions provides new efficient access to N-H indoline derivatives, demonstrating the high potential of auto-tandem catalysis with a Brønsted base as a methodology for organic synthesis.

Original languageEnglish
Pages (from-to)5309-5313
Number of pages5
JournalOrganic letters
Volume20
Issue number17
DOIs
Publication statusPublished - 2018 Sep 7

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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