Stereoselective synthesis of chiral thiol-containing 1,2-aminoalcohols via SmI2-mediated coupling

Carina Doler, Michael Friess, Florian Lackner, Hansjörg Weber, Roland C. Fischer, Rolf Breinbauer*

*Corresponding author for this work

Research output: Contribution to journalArticle

Abstract

The stereoselective synthesis of highly functionalized aminohydroxythiols represents a synthetic challenge as the oxidation sensitivity and coordinating property of the thiol group interferes with many established synthetic methods. The SmI2/LiBr-mediated reductive coupling between Ellman N-sulfinylimines, containing thiol groups protected either as trityl thioether or dihydrothiazolidine, and aldehydes enables the synthesis of chiral aminohydroxythiols in high enantio- and diastereoselectivity. The scope of this reaction has been established for 18 examples and applied for the synthesis of a complex intermediate needed for a biosynthesis study.

Original languageEnglish
Article number131249
JournalTetrahedron
Volume76
Issue number51
DOIs
Publication statusPublished - 18 Dec 2020

Keywords

  • Asymmetric synthesis
  • Chiral auxiliary
  • Ellman reagent
  • Reductive coupling
  • Samarium diiodide
  • Sharpless aminohydroxylation
  • Single electron transfer

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fields of Expertise

  • Human- & Biotechnology

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