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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 language | English |
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Article number | 131249 |
Journal | Tetrahedron |
Volume | 76 |
Issue number | 51 |
DOIs | |
Publication status | Published - 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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Dive into the research topics of 'Stereoselective synthesis of chiral thiol-containing 1,2-aminoalcohols via SmI2-mediated coupling'. Together they form a unique fingerprint.Projects
- 1 Finished
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FWF - RETROBIO - A twofold retrosynthetic implementation of a novel biochemical pathway (RETROBIO)
1/10/14 → 30/09/18
Project: Research project