Iron- and Organo-Catalyzed Borrowing Hydrogen for the Stereoselective Construction of Tetrahydropyrans

Organic Letters, Год журнала: 2024, Номер 26(27), С. 5788 - 5793

Опубликована: Июнь 27, 2024

Stereocontrolled oxa-Michael additions are challenging, given the high reversibility of process, which ultimately leads to racemization newly formed stereocenters. When iron-catalyzed borrowing hydrogen from allylic alcohols was combined with a stereocontrolled organocatalytic addition, wide array chiral tetrahydropyrans were efficiently prepared. The reaction could be performed in diastereoselective manner pre-existing stereocenters or enantioselectively achiral substrates. key success reactivity iron complex, selective for alcohol dehydrogenation and irreversibly led final product.

Язык: Английский

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CO to Isonitrile Substitution in Iron Cyclopentadienone Complexes: A Class of Active Iron Catalysts for Borrowing Hydrogen Strategies

ACS Catalysis, Год журнала: 2024, Номер 14(10), С. 7795 - 7805

Опубликована: Май 6, 2024

Discovering active, cheap iron complexes for eco-compatible borrowing hydrogen transformations constitutes a real challenge. In this context, we developed family of isonitrile-substituted cyclopentadienone complexes. They were successfully applied in traditional amine alkylation with alcohols and, notably, the development photoactivated multicatalytic enantioselective allylic alcohol functionalization. Of importance, catalyst showing greater activity under photoirradiation differs from one most active conventional using chemical activation. This underscores importance incorporating isonitrile ligands readily customizable manner, resulting catalysts complementary reactivities. The characterization their physical properties was complemented by density functional theory calculations to enhance our understanding behavior. Given distinctive disclosed catalysts, application is poised pave way exploring challenging reactivities related catalytic processes.

Язык: Английский

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Visible Light Mediated Iron‐Catalyzed One‐Pot Synthesis of Chromenopyrroles from Benzyl Alcohols, 2‐Hydroxyacetophenones and Methyl/Ethyl Isocyanoacetate at Room Temperature

ChemistrySelect, Год журнала: 2024, Номер 9(37)

Опубликована: Сен. 30, 2024

Abstract An effective, facile, trivial, and one‐pot procedure for the synthesis of chromenopyrroles from benzyl alcohols, 2‐hydroxyacetophenones, methyl/ethyl isocyanoacetate at room temperature in presence visible light has been developed. The Ag salt plays an important role activation cyclization step. Air‐stable low‐cost Knölker iron complex utilized dehydrogenation primary alcohols that would typically require a higher temperature. established protocol is scalable extensive functional group tolerance, generating good to excellent yields

Язык: Английский

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Six-membered ring systems: With O and/or S atoms

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 421 - 484

Опубликована: Янв. 1, 2024

Язык: Английский

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Iodine catalyzed one-pot three-step synthesis of isoxazoles from primary alcohols and 3-O-propargyl flavones using DMSO as the oxidant

Tetrahedron Letters, Год журнала: 2023, Номер 131, С. 154799 - 154799

Опубликована: Окт. 15, 2023

Язык: Английский

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