Directed Dehydrogenative Copper‐Catalyzed C−H Thiolation in Pseudo‐Anomeric Position of Glycals using Thiol and Thiosugar Partners

LI, Linlin; Mahri, Lynda; Robichon, Morgane de; Fatthalla, Maha I.; Ferry, Angélique; Messaoudi, Samir

doi:10.1002/adsc.202200557

Adv Synth Catal

2022

DOI: 10.1002/adsc.202200557

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Directed Dehydrogenative Copper‐Catalyzed C−H Thiolation in Pseudo‐Anomeric Position of Glycals using Thiol and Thiosugar Partners

Linlin LI

Lynda Mahri

Morgane de Robichon

et al.

Abstract: The synthesis of 1-thiotrehaloses and thioglycals by a directed copper-catalyzed dehydrogenative CÀ H thiolation of the pseudo-anomeric bond of glycals is described. The use of aminoquinoline-containing glycals as well as thiosugars or thiols as coupling partners led to the synthesis of a library of thioglycosides in moderate to good yields.

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Cited by 4 publications

References 63 publications

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Copper‐Mediated C−H Chalcogenation of Heterocycles: Application to the Synthesis of Chalcogenoxanthones

Zhou¹,

Zheng

et al. 2023

Adv Synth Catal

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A copper‐mediated C(sp2)‒H chalcogenation of heterocycles with readily available dichalcogenide, benzeneselenol and thiol is described. This protocol demonstrates scalability, good chemo‐ and regio‐selectivity, as well as broad functional group tolerance, which overall provides an accessible method to valuable aryl chalcogenides. The chalcogenated picolinamide products could be further transformed into selenoxanthones and thioxanthone scaﬀolds through intramolecular cyclization via a semi‐one pot process.

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Copper‐Mediated C−H Chalcogenation of Heterocycles: Application to the Synthesis of Chalcogenoxanthones

Zhou¹,

Zheng

et al. 2023

Adv Synth Catal

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Ferrier/Aza‐Wacker/Epoxidation/Glycosylation (FAWEG) Sequence to Access 1,2‐Trans 3‐Amino‐3‐deoxyglycosides

Geulin

Bourne‐Branchu

Ayed

et al. 2023

Chemistry A European J

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3‐Amino‐3‐deoxyglycosides constitute an essential class of nitrogen‐containing sugars. Among them, many important 3‐amino‐3‐deoxyglycosides possess a 1,2‐trans relationship. In view of their numerous biological applications, the synthesis of 3‐amino‐3‐deoxyglycosyl donors giving rise to a 1,2‐trans glycosidic linkage is thus an important challenge. Even though glycals are highly polyvalent donors, the synthesis and reactivity of 3‐amino‐3‐deoxyglycals have been little studied. In this work, we describe a new sequence, involving a Ferrier rearrangement and subsequent aza‐Wacker cyclization that allows the rapid synthesis of orthogonally protected 3‐amino‐3‐deoxyglycals. Finally a 3‐amino‐3‐deoxygalactal derivative was submitted for the first time to an epoxidation/glycosylation with high yield and great diastereoselectivity, highlighting FAWEG (Ferrier/Aza‐Wacker/Epoxidation/Glycosylation) as a new approach to access 1,2‐trans 3‐amino‐3‐deoxyglycosides.

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Copper‐Mediated Cross‐Dehydrogenative Coupling Reaction of Pyrrole and Indole Derivatives with Thiols

Ma,

Xu,

et al. 2024

Eur J Org Chem

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A copper‐mediated C(sp2)–H thiolations of pyrrole and indole derivatives with commercially available thiols utilizing removable monodentate directing group is described. This protocol tolerated a broad functional group, providing the thiolated products in 40%‐97% yields. Furthermore, the synthetic utility of this protocol was demonstrated by the late‐ stage functionalization of bioactive tryptophan peptide. Preliminary mechanistic studies indicated that a Cu(II)/Cu(III) reaction model is most likely to be involved in this C–H thiolation.

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Directed Dehydrogenative Copper‐Catalyzed C−H Thiolation in Pseudo‐Anomeric Position of Glycals using Thiol and Thiosugar Partners

Cited by 4 publications

References 63 publications

Copper‐Mediated C−H Chalcogenation of Heterocycles: Application to the Synthesis of Chalcogenoxanthones

Copper‐Mediated C−H Chalcogenation of Heterocycles: Application to the Synthesis of Chalcogenoxanthones

Ferrier/Aza‐Wacker/Epoxidation/Glycosylation (FAWEG) Sequence to Access 1,2‐Trans 3‐Amino‐3‐deoxyglycosides

Copper‐Mediated Cross‐Dehydrogenative Coupling Reaction of Pyrrole and Indole Derivatives with Thiols

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