Direct Catalytic Asymmetric Aldol Reaction of Thioamide with an α-Vinyl Appendage

Jin Cui, Akimichi Ohtsuki, Takumi Watanabe, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

The direct catalytic asymmetric aldol reaction is an emerging catalytic methodology that provides atom-economical access to functionalized chiral building blocks. Thioamides are useful aldol donors due to their high-fidelity chemoselective enolization and divergent post-aldol transformations. Herein we describe the incorporation of an α-vinyl appendage on a thioamide, which expands the utility of aldol adducts for natural product synthesis. This vinylated thioamide was not accommodated under the previously identified catalyst settings, but the newly developed catalytic conditions furnished aldol products containing the pendant vinyl group.

Original languageEnglish
Pages (from-to)2598-2601
Number of pages4
JournalChemistry - A European Journal
Volume24
Issue number11
DOIs
Publication statusPublished - 2018 Feb 21
Externally publishedYes

Keywords

  • aldol reactions
  • asymmetric catalysis
  • cooperative catalysis
  • formal synthesis
  • thioamide

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Direct Catalytic Asymmetric Aldol Reaction of Thioamide with an α-Vinyl Appendage'. Together they form a unique fingerprint.

Cite this