Chiral 1-(1,3-dithian-2-yl) prop-2-en-1-ols: new scaffolds for enantiopure α-hydroxyaldehydes

Masaru Akehi, Mariko Kawamoto, Tadakatsu Mandai

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Abstract We have demonstrated that chiral 1-(1,3-dithian-2-yl)prop-2-en-1-ols as new scaffolds, obtained by enzyme-catalyzed kinetic resolution, undergo Suzuki-Miyaura cross-couplings and hydroformylation smoothly. Also, we have found that a 1,3-dithianyl group of the products can be removed without any erosion of the enantiopurity under mild conditions. A new access to a variety of enantiopure α-hydroxyaldehydes with ensured absolute configuration is described.

Original languageEnglish
Article number26757
Pages (from-to)6488-6498
Number of pages11
JournalTetrahedron
Volume71
Issue number37
DOIs
Publication statusPublished - Aug 7 2015
Externally publishedYes

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Hydroformylation
Enzyme kinetics
Scaffolds
Erosion
Enzymes

Keywords

  • 1,3-Dipolar cycloaddition
  • Hydroformylation
  • Scaffold
  • Suzuki-Miyaura cross-coupling
  • α-Hydroxyaldehyde

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Chiral 1-(1,3-dithian-2-yl) prop-2-en-1-ols : new scaffolds for enantiopure α-hydroxyaldehydes. / Akehi, Masaru; Kawamoto, Mariko; Mandai, Tadakatsu.

In: Tetrahedron, Vol. 71, No. 37, 26757, 07.08.2015, p. 6488-6498.

Research output: Contribution to journalArticle

Akehi, Masaru ; Kawamoto, Mariko ; Mandai, Tadakatsu. / Chiral 1-(1,3-dithian-2-yl) prop-2-en-1-ols : new scaffolds for enantiopure α-hydroxyaldehydes. In: Tetrahedron. 2015 ; Vol. 71, No. 37. pp. 6488-6498.
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