Direct conversion of amino acids to oxetanol bioisosteres <i>via</i> photoredox catalysis

Delos Reyes, Avelyn Mae V.; Nieves Escobar, Christopher S.; Muñoz, Alberto; Huffman, Maya I.; Tan, Derek S.

doi:10.1039/d3sc00936j

Cited by 9 publications

(1 citation statement)

References 51 publications

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“…Compared to conventional approaches, photocatalysis often proceeds through a mechanistic pathway that involves a radical and operates under mild conditions, rendering otherwise unreactive substrates productive and affording superior functionality tolerance. Alkanes, carboxyl acids, alkyl halides, olefins, ketones, and others have become viable precursors for the synthesis of tertiary alcohols from ketones under photocatalysis (Scheme b). However, a direct deoxygenative addition of alcohols to ketones remains elusive.…”

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confidence: 99%

Photoredox and NHC Enabled Deoxygenative Alcohol Homologation via Formal 1,2-Addition

Song,

Li,

Wang

et al. 2023

Org. Lett.

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A highly efficient photoinduced iron-catalyzed method has been developed for the direct use of alcohols as surrogates for organometallic reagents in the synthesis of tertiary alcohols. This method can be applied to both primary and secondary alcohols with diverse structures, enabling their reaction with aryl ketones under mild conditions. A variety of functional groups, including those that are typically reactive under conventional tertiary alcohol synthesis conditions, are compatible. Mechanistically, this reaction proceeds through the direct addition of the radical to the carbonyl pathway.

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confidence: 99%

Photoredox and NHC Enabled Deoxygenative Alcohol Homologation via Formal 1,2-Addition

Song,

Li,

Wang

et al. 2023

Org. Lett.

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O‐p‐Methoxyphenyl α‐Hydroxycarboxylic Acids as Versatile Hydroxyalkylation Agents for Photocatalysis

Nopper,

Veith,

Himmelsbach

et al. 2024

Chemistry A European J

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Reliable radical precursors are crucial for photocatalytic processes. In particular, heteroatom‐stabilized radicals have attracted considerable research interest in photocatalysis. Among them, α‐amino radicals have received the most attention, while the research on α‐hydroxy radicals is much less developed. Herein, we present O‐PMP α‐hydroxycarboxylic acids as novel precursors for the formation of oxygen‐stabilized radicals. These radicals have been successfully used as building blocks in Pd‐catalyzed allylation reactions, Ni‐catalyzed arylation and alkenylation reactions, and Giese reactions. A subsequent deprotection step liberates the corresponding hydroxyalkylation products.

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Physicochemical and Biological Evaluation of gem‐Difluorinated Saturated Oxygen Heterocycles as Bioisosteres for Drug Discovery

Melnykov,

Liashuk,

Holovach

et al. 2024

Chemistry A European J

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A comprehensive study on the physicochemical properties of gem‐fluorinated O‐heterocyclic substituents is reported. Systematic additive effects of introducing O‐ and gem‐CF2 group introduction on acidic properties (pKa) of the corresponding carboxylic acids / protonated primary amines was demonstrated. The impact of the O/CF2 moieties on lipophilicity (LogP) were found to be complex; significant mutual influence of the corresponding polar moieties governed the compound’s overall properties in this case. Biological evaluation of MAPK kinase inhibitors incorporating the title substituents demonstrated their utility as promising fragments for bioisosteric replacements in drug discovery campaigns.

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Direct conversion of amino acids to oxetanol bioisosteres via photoredox catalysis

Abstract: Carboxylic acids can be converted directly to bioisosteric 3-oxetanols by leveraging the unique reactivity of photoredox catalysis. Cr-mediated and Cr-free variants of the reaction have been developed, both having quantum yields greater than 5.

Cited by 9 publications

References 51 publications

Photoredox and NHC Enabled Deoxygenative Alcohol Homologation via Formal 1,2-Addition

Photoredox and NHC Enabled Deoxygenative Alcohol Homologation via Formal 1,2-Addition

O‐p‐Methoxyphenyl α‐Hydroxycarboxylic Acids as Versatile Hydroxyalkylation Agents for Photocatalysis

Physicochemical and Biological Evaluation of gem‐Difluorinated Saturated Oxygen Heterocycles as Bioisosteres for Drug Discovery

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