Direct Catalytic Asymmetric 1,6-Conjugate Addition of Amides to p-Quinone Methides

Zhongdong Sun, Bo Sun, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

Amide pronucleophiles were successfully incorporated into a 1,6-conjugate addition reaction manifold using p-quinone methides (p-QMs) as electrophiles. Four different types of functionalities were tolerated as α-substituents of the amides, allowing for expeditious access to a range of enantiomerically enriched diarylmethine products. The 7-azaindoline unit is critically important for in situ catalytic enolization of the amide pronucleophile, engaging in 1,6-conjugate addition to p-QMs with readily available catalyst components.

Original languageEnglish
Pages (from-to)3070-3073
Number of pages4
JournalOrganic Letters
Volume20
Issue number10
DOIs
Publication statusPublished - 2018 May 18
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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