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*

*Korrespondierende/r Autor/in für diese Arbeit

Publikation: Beitrag in einer FachzeitschriftArtikel

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.

Originalspracheenglisch
Aufsatznummer131249
FachzeitschriftTetrahedron
DOIs
PublikationsstatusAngenommen/In Druck - 1 Jan 2020

ASJC Scopus subject areas

  • !!Biochemistry
  • !!Drug Discovery
  • Organische Chemie

Fields of Expertise

  • Human- & Biotechnology

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