Rearrangement of thiazolidine derivatives – a synthesis of a chiral fused oxathiane–γ-lactam bicyclic system

Karolina Kamińska; Dominika Iwan; Jakub Trojnar; Marek Daszkiewicz; Joanna E. Rode; Jacek Wojaczyński; Elżbieta Wojaczyńska

doi:10.1039/D3OB01454A

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Rearrangement of thiazolidine derivatives – a synthesis of a chiral fused oxathiane–γ-lactam bicyclic system†

Karolina Kamińska,*^a Dominika Iwan,^a Jakub Trojnar,^a Marek Daszkiewicz,

^b Joanna E. Rode,

^c Jacek Wojaczyński

^d and Elżbieta Wojaczyńska

*^a

Author affiliations

* Corresponding authors

^a Faculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland
E-mail: kaminska.karolinazofia@gmail.com, elzbieta.wojaczynska@pwr.edu.pl

^b Institute of Low Temperature and Structure Research, Polish Academy of Sciences, Okólna St. 2, 50-422 Wrocław, Poland

^c Institute of Nuclear Chemistry and Technology, Dorodna St. 16, 03-195 Warszawa, Poland

^d Faculty of Chemistry, University of Wrocław, F. Joliot-Curie St. 14, 50-383 Wrocław, Poland

Abstract

Reaction of L-cysteine with carbonyl compounds leads to thiazolidine derivatives which undergo a stereoselective conversion to two types of chiral bicyclic products bearing two or three stereogenic centers, including the first fused oxathiane–γ-lactam system.

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DOI: https://doi.org/10.1039/D3OB01454A
Article type: Paper
Submitted: 10 Sep 2023
Accepted: 06 Nov 2023
First published: 06 Nov 2023
This article is Open Access

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Org. Biomol. Chem., 2023,21, 9182-9191

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Rearrangement of thiazolidine derivatives – a synthesis of a chiral fused oxathiane–γ-lactam bicyclic system

K. Kamińska, D. Iwan, J. Trojnar, M. Daszkiewicz, J. E. Rode, J. Wojaczyński and E. Wojaczyńska, Org. Biomol. Chem., 2023, 21, 9182 DOI: 10.1039/D3OB01454A

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Organic & Biomolecular Chemistry

Rearrangement of thiazolidine derivatives – a synthesis of a chiral fused oxathiane–γ-lactam bicyclic system†

Abstract

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Rearrangement of thiazolidine derivatives – a synthesis of a chiral fused oxathiane–γ-lactam bicyclic system

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