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 journalArticlepeer-review

94 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
Externally publishedYes

All Science Journal Classification (ASJC) codes

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

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