Brønsted Base-Catalyzed Reductive Cyclization
of Alkynyl α‑Iminoesters through Auto-Tandem Catalysis
Version 2 2018-08-15, 20:32
Version 1 2018-08-15, 20:30
Posted on 2018-08-15 - 20:32
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.
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Kondoh, Azusa; Terada, Masahiro (2018). Brønsted Base-Catalyzed Reductive Cyclization
of Alkynyl α‑Iminoesters through Auto-Tandem Catalysis. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.8b02236
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