Direct Catalytic Asymmetric Aldol Reaction of α-Vinyl Acetamide

Toshifumi Takeuchi, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

A direct catalytic asymmetric aldol addition of an α-vinyl 7-azaindoline amide to both aromatic and aliphatic aldehydes was promoted by a cooperative acid/base catalyst in a stereodivergent manner. The key structural element, a 7-azaindoline moiety, facilitated catalytic enolization, allowing for subsequent stereoselective aldol addition. Enantioselective synthesis of the key intermediate of blumiolide C and kainic acid supported the synthetic utility of this protocol.

Original languageEnglish
Pages (from-to)5851-5858
Number of pages8
JournalJournal of Organic Chemistry
Volume83
Issue number10
DOIs
Publication statusPublished - 2018 May 18
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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