Hexafluoroisopropanol-Induced Facial Selectivity in a Hindered Diels–Alder Reaction - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Synthesis: Journal of Synthetic Organic Chemistry Année : 2023

Hexafluoroisopropanol-Induced Facial Selectivity in a Hindered Diels–Alder Reaction

Résumé

BRD4780 is a small molecule that can selectively clear mutant MUC1-fs protein in mucin kidney disease models. Prior syntheses of BRD4780 were unsuitable for preparation on large scale. In this manuscript, HFIP is described as a unique solvent that allowed the key Diels–Alder reaction to proceed with >20:1 endo diastereoselectivity, enabling the kg-scale preparation of BRD4780 for further studies.

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Chimie organique
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Dates et versions

hal-04225639 , version 1 (03-10-2023)

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David Kornfilt, Brian Chamberlain, Isabelle Chataigner, Riccardo Spezia, Florence Wagner. Hexafluoroisopropanol-Induced Facial Selectivity in a Hindered Diels–Alder Reaction. Synthesis: Journal of Synthetic Organic Chemistry, 2023, 55 (13), pp.2047-2052. ⟨10.1055/a-2016-4548⟩. ⟨hal-04225639⟩
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