A designed amide as an aldol donor in the direct catalytic asymmetric aldol reaction

Karin Weidner, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

45 Citations (Scopus)

Abstract

The direct catalytic asymmetric aldol reaction offers efficient access to β-hydroxy carbonyl entities. Described is a robust direct catalytic asymmetric aldol reaction of α-sulfanyl 7-azaindolinylamide, thus affording both aromatic and aliphatic β-hydroxy amides with high ee values. The design of this transformation features a cooperative interplay of a soft and a hard Lewis acid, which together facilitate the challenging chemoselective enolization by a hard Brønsted base.

Original languageEnglish
Pages (from-to)6150-6154
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number24
DOIs
Publication statusPublished - 2014 Jun 10
Externally publishedYes

Keywords

  • aldol reaction
  • amides
  • asymmetric catalysis
  • silver
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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