Iron- and organo-catalyzed borrowing hydrogen for the stereoselective construction of tetrahydropyrans - BIG - Chimie et Biologie des Métaux (CBM)
Article Dans Une Revue Organic Letters Année : 2024

Iron- and organo-catalyzed borrowing hydrogen for the stereoselective construction of tetrahydropyrans

Résumé

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

Domaines

Chimie
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Dates et versions

hal-04683677 , version 1 (02-09-2024)

Identifiants

Citer

Anestis Alexandridis, Thibault Rancon, Abigail Halliday, Amélie Kochem, Adrien Quintard. Iron- and organo-catalyzed borrowing hydrogen for the stereoselective construction of tetrahydropyrans. Organic Letters, 2024, 26 (27), pp.5788-5793. ⟨10.1021/acs.orglett.4c01969⟩. ⟨hal-04683677⟩
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