Direct Catalytic Asymmetric Aldol Reaction of α-Alkylamides

Zijian Liu, Toshifumi Takeuchi, Roman Pluta, Fernando Arteaga Arteaga, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

A catalytic asymmetric aldol reaction directly employing amides as latent enolates has remained elusive because of the resistance of amides to enolization. A direct aldol reaction of α-alkylamides without any electron-withdrawing group harnessed by specific activation of 7-azaindoline amides under soft Lewis acid/Brønsted base cooperative catalysis is reported. Diastereo- and enantioselective coupling with ynals and aromatic aldehydes as well as divergent functional group interconversion of the amide provided expeditious access to a variety of aliphatic and aromatic chiral building blocks.

Original languageEnglish
Pages (from-to)710-713
Number of pages4
JournalOrganic Letters
Volume19
Issue number3
DOIs
Publication statusPublished - 2017 Feb 3
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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