Enantioselective acyl transfer catalysis by a combination of common catalytic motifs and electrostatic interactions

Hiroki Mandai, Kazuki Fujii, Hiroshi Yasuhara, Kenko Abe, Koichi Mitsudo, Toshinobu Korenaga, Seiji Suga

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

Catalysts that can promote acyl transfer processes are important to enantioselective synthesis and their development has received significant attention in recent years. Despite noteworthy advances, discovery of small-molecule catalysts that are robust, efficient, recyclable and promote reactions with high enantioselectivity can be easily and cost-effectively prepared in significant quantities (that is, >10 g) has remained elusive. Here, we demonstrate that by attaching a binaphthyl moiety, appropriately modified to establish H-bonding interactions within the key intermediates in the catalytic cycle, and a 4-aminopyridyl unit, exceptionally efficient organic molecules can be prepared that facilitate enantioselective acyl transfer reactions. As little as 0.5 mol% of a member of the new catalyst class is sufficient to generate acyl-substituted all-carbon quaternary stereogenic centres in quantitative yield and in up to 98:2 enantiomeric ratio (er) in 5 h. Kinetic resolution or desymmetrization of 1,2-diol can be performed with high efficiency and enantioselectivity as well.

Original languageEnglish
Article number11297
JournalNature Communications
Volume7
DOIs
Publication statusPublished - Apr 15 2016

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Coulomb interactions
Static Electricity
Catalysis
catalysis
Carbon
Enantioselectivity
electrostatics
Costs and Cost Analysis
catalysts
Catalysts
Molecules
interactions
molecules
costs
cycles
Kinetics
carbon
kinetics
synthesis
Costs

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Chemistry(all)
  • Physics and Astronomy(all)

Cite this

Enantioselective acyl transfer catalysis by a combination of common catalytic motifs and electrostatic interactions. / Mandai, Hiroki; Fujii, Kazuki; Yasuhara, Hiroshi; Abe, Kenko; Mitsudo, Koichi; Korenaga, Toshinobu; Suga, Seiji.

In: Nature Communications, Vol. 7, 11297, 15.04.2016.

Research output: Contribution to journalArticle

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AU - Korenaga, Toshinobu

AU - Suga, Seiji

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