Direct catalytic asymmetric aldol reaction of thioamides

A concise asymmetric synthesis of (R)-fluoxetine

Mitsutaka Iwata, Ryo Yazaki, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

A direct catalytic asymmetric aldol reaction of aromatic aldehydes and thioamides is described. A soft Lewis acid/hard Brønsted base cooperative catalyst comprising (R,R)-Ph-BPE/[Cu(CH3CN)4]PF 6/Li(OC6H4-p-OMe) promoted the title reaction efficiently, triggered by in situ generation of the active thioamide enolate through a soft-soft interaction of Cu(I) and the thioamide. The aldol product was transformed into (R)-fluoxetine, an antidepressant agent.

Original languageEnglish
Pages (from-to)1688-1694
Number of pages7
JournalTetrahedron Asymmetry
Volume21
Issue number13-14
DOIs
Publication statusPublished - Jun 2 2010
Externally publishedYes

Fingerprint

Thioamides
Fluoxetine
Aldehydes
Catalysts
Acids
synthesis
aldehydes
Lewis Acids
catalysts
Antidepressive Agents
acids
products
interactions
3-hydroxybutanal

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Direct catalytic asymmetric aldol reaction of thioamides : A concise asymmetric synthesis of (R)-fluoxetine. / Iwata, Mitsutaka; Yazaki, Ryo; Kumagai, Naoya; Shibasaki, Masakatsu.

In: Tetrahedron Asymmetry, Vol. 21, No. 13-14, 02.06.2010, p. 1688-1694.

Research output: Contribution to journalArticle

Iwata, Mitsutaka ; Yazaki, Ryo ; Kumagai, Naoya ; Shibasaki, Masakatsu. / Direct catalytic asymmetric aldol reaction of thioamides : A concise asymmetric synthesis of (R)-fluoxetine. In: Tetrahedron Asymmetry. 2010 ; Vol. 21, No. 13-14. pp. 1688-1694.
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