Highly Stereoselective (3+2) Cycloadditions of Levoglucosenone (LGO) with the In Situ-Generated Thiocarbonyl

Grzegorz Mlostoń, Małgorzata Celeda, Marcin Palusiak, Heinz Heimgartner, Zbigniew J Witczak

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Article in Molecules (Basel, Switzerland), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 authors.

Grzegorz MlostońDepartment of Organic and Applied Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, Poland.ORCID 0000-0003-3631-3239

Małgorzata CeledaDepartment of Organic and Applied Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, Poland.

Marcin PalusiakDepartment of Physical Chemistry, Faculty of Chemistry, University of Lodz, Pomorska 163/165, 90-236 Lodz, Poland.ORCID 0000-0002-0032-0878

Heinz HeimgartnerDepartment of Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.ORCID 0000-0002-5145-4251

Zbigniew J WitczakDepartment of Pharmaceutical Sciences, Nesbitt School of Pharmacy, Wilkes University, 84 W. South Street, Wilkes-Barre, PA 18766, USA.ORCID 0000-0003-3310-6808

Funding

University of Lodz, Poland Grant-IDUB 2020-2023

6 · The paper itself

Abstract

The in situ-generated thiocarbonyl S-methanides derived from cycloaliphatic thioketones undergo (3+2) cycloaddition onto the C=C bond of levoglucosenone yielding anticipated, polycyclic tetrahydrothiophene derivatives in a regio- and stereoselective manner. The cycloaddition process occurred stereoselectively via the less hindered exo-face approach; exo-diastereoisomers were formed in all studied reactions. Some of the obtained crystalline (3+2) cycloadducts were studied by the monocrystal X-ray diffraction analysis, which unambiguously confirmed the postulated structure. Stable (3+2) cycloadducts were isolated in good yields (50-80%).

Indexed as

(3+2) cycloadditionslevoglucosenonesingle-crystal X-ray analysissulfur heterocyclesthiocarbonyl S-methanides

Identifiers

PMID42451569

DOI10.3390/molecules31132198

PMCPMC13363599

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