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Article Dans Une Revue Angewandte Chemie International Edition Année : 2020

Asymmetric Transfer Hydrogenation of gem ‐Difluorocyclopropenyl Esters: Access to Enantioenriched gem ‐Difluorocyclopropanes

Résumé

A catalytic enantioselective access to disubstituted functionalized gem-difluorocyclopropanes, which lie among emerging fluorinated motifs, was developed by asymmetric transfer hydrogenation of gem-difluorocyclopropenyl esters, catalyzed by Noyori-Ikariya (p-cymene)-ruthenium(II) complex, with (N-tosyl-1,2-diphenylethylenediamine) as chiral ligand and isopropanol as hydrogen donor. The resulting cis-gem-difluorocyclopropyl esters were obtained with moderate to high enantiomeric purities (ee = 66-99%) and post-functionalization reactions enable access to valuable building blocks incorporating a cis-or trans-gemdifluorocyclopropyl motif.

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Chimie
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hal-03439559 , version 1 (22-11-2021)

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Khalil Yamani, Hugo Pierre, Alexis Archambeau, Christophe Meyer, Janine Cossy. Asymmetric Transfer Hydrogenation of gem ‐Difluorocyclopropenyl Esters: Access to Enantioenriched gem ‐Difluorocyclopropanes. Angewandte Chemie International Edition, 2020, 59 (42), pp.18505 - 18509. ⟨10.1002/anie.202008572⟩. ⟨hal-03439559⟩
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