Diastereoselective access to C,C-glycosyl amino acids via iron-catalyzed, auxiliary-enabled MHAT coupling

Lang, Mylène; Tardieu, Damien; Pousse, Benoit; Compain, Philippe; Kern, Nicolas

doi:10.1039/d3cc06249j

Chem. Commun.

2024

DOI: 10.1039/d3cc06249j

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Diastereoselective access to C,C-glycosyl amino acids via iron-catalyzed, auxiliary-enabled MHAT coupling

Mylène Lang,

Damien Tardieu,

Benoit Pousse

et al.

Abstract: Access to C,C-glycosyl aminoacids as a novel class of glycomimetics is reported by means of radical generation, intermolecular addition and stereoselective reduction via a metal-induced hydrogen atom transfer (MHAT) sequence....

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Cited by 2 publications

References 68 publications

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Glycosyl Radical-Based Synthesis of C-Alkyl Glycosides Bearing a Cyclopropane via a Deoxygenative Giese Addition–Reduction–Cyclization Cascade

Pang,

Feng,

Zhang

et al. 2024

Org. Lett.

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Glycosyl Radical-Based Synthesis of C-Alkyl Glycosides Bearing a Cyclopropane via a Deoxygenative Giese Addition–Reduction–Cyclization Cascade

Pang,

Feng,

Zhang

et al. 2024

Org. Lett.

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Iron-catalyzed radical Markovnikov hydrohalogenation and hydroazidation of alkenes

Elfert,

Frye,

Rempel

et al. 2024

Nat Commun

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We herein report radical hydroazidation and hydrohalogenation of mono-, di- and trisubstituted alkenes through iron catalysis. The alkene moiety that often occurs as a functionality in natural products is readily transformed into useful building blocks through this approach. Commercially available tosylates and α-halogenated esters are used as radical trapping reagents in combination with silanes as reductants. The reported radical Markovnikov hydroazidation, hydrobromination, hydrochlorination, and hydroiodination occur under mild conditions. These hydrofunctionalizations are valuable and practical alternatives to ionic hydrohalogenations with the corresponding mineral acids that have to be run under harsher acidic conditions, which diminishes the functional group tolerance. Good to excellent diastereoselectivities can be obtained for the hydrofunctionalization of cyclic alkenes.

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Diastereoselective access to C,C-glycosyl amino acids via iron-catalyzed, auxiliary-enabled MHAT coupling

Abstract: Access to C,C-glycosyl aminoacids as a novel class of glycomimetics is reported by means of radical generation, intermolecular addition and stereoselective reduction via a metal-induced hydrogen atom transfer (MHAT) sequence....

Cited by 2 publications

References 68 publications

Glycosyl Radical-Based Synthesis of C-Alkyl Glycosides Bearing a Cyclopropane via a Deoxygenative Giese Addition–Reduction–Cyclization Cascade

Glycosyl Radical-Based Synthesis of C-Alkyl Glycosides Bearing a Cyclopropane via a Deoxygenative Giese Addition–Reduction–Cyclization Cascade

Iron-catalyzed radical Markovnikov hydrohalogenation and hydroazidation of alkenes

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