Direct Catalytic Asymmetric Mannich-Type Reaction of Alkylamides

Fernando Arteaga Arteaga, Zijian Liu, Lennart Brewitz, Jianyang Chen, Bo Sun, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

Direct enolate formation coupled with subsequent enantioselective C-C bond formation remains a topic of intense interest in asymmetric catalysis. This methodology is achieved even with low acidic amides without an electron-withdrawing group at the α-position in the context of a Mannich-type reaction. Acetate-, propionate-, and butyrate-type 7-azaindoline amides served as enolate precursors to afford the desired Mannich adducts with high stereoselectivity, and ligand-enabled diastereo-divergency provided access to both anti/syn diastereomers. The facile transformation of the amide moiety ensures the synthetic utility of the Mannich adducts.

Original languageEnglish
Pages (from-to)2391-2394
Number of pages4
JournalOrganic Letters
Volume18
Issue number10
DOIs
Publication statusPublished - 2016 May 20
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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