Direct catalytic asymmetric aldol reactions of thioamides: Toward a stereocontrolled synthesis of 1,3-polyols

Mitsutaka Iwata, Ryo Yazaki, Yuta Suzuki, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticle

87 Citations (Scopus)

Abstract

(Chemical Equation Presented) A direct catalytic asymmetric aldol reaction of thioamides with a soft Lewis acid/hard Brønsted base cooperative catalytic system comprising (R,R)-Ph-BPE/[Cu(CH3CN) 4]PF6/LiOAr is described. Highly chemoselective deprotonative activation of thioamides allows for a direct aldol reaction of α-nonbranched aliphatic aldehydes, which are susceptible to self-condensation. Facile reduction of the thioamide functionality and a catalyst-controlled second aldol reaction provides 1,3-diols in a highly stereoselective manner.

Original languageEnglish
Pages (from-to)18244-18245
Number of pages2
JournalJournal of the American Chemical Society
Volume131
Issue number51
DOIs
Publication statusPublished - Dec 30 2009

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Thioamides
Polyols
Aldehydes
Condensation
Chemical activation
Catalysts
Acids
Lewis Acids
polyol
3-hydroxybutanal

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Direct catalytic asymmetric aldol reactions of thioamides : Toward a stereocontrolled synthesis of 1,3-polyols. / Iwata, Mitsutaka; Yazaki, Ryo; Suzuki, Yuta; Kumagai, Naoya; Shibasaki, Masakatsu.

In: Journal of the American Chemical Society, Vol. 131, No. 51, 30.12.2009, p. 18244-18245.

Research output: Contribution to journalArticle

Iwata, Mitsutaka ; Yazaki, Ryo ; Suzuki, Yuta ; Kumagai, Naoya ; Shibasaki, Masakatsu. / Direct catalytic asymmetric aldol reactions of thioamides : Toward a stereocontrolled synthesis of 1,3-polyols. In: Journal of the American Chemical Society. 2009 ; Vol. 131, No. 51. pp. 18244-18245.
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