Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2021, Issue 8, Pages 1249-1257Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202001493
Keywords
Chiral ligands; Desymmetrization; Enantioselective reaction; Epoxides; Lewis acid
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Funding
- Czech Science Foundation [17-07707S]
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This study presents a catalytic and highly enantioselective ring-opening reaction of epoxides, utilizing newly designed chiral bipyridine ligands. A Sc-complex with a newly developed bipyridine ligand demonstrated high reactivity and stereocontrol in the desymmetrization of meso-epoxides with various alcohols, achieving enantioenriched 1,2-alkoxyalcohols with high e.r. values. Additionally, attempted ring-opening of meso-epoxides with anilines showed lower enantioselectivity, dependent on the electronic effect of substituents on the aromatic ring.
The ring-opening of epoxides is a synthetically significant process widely applied in all kinds of chemistry. Herein, we report the catalytic and highly enantioselective variant of this reaction exploiting our recent endeavors to design and synthesize chiral bipyridine type ligands. A Sc-complex with a newly developed bipyridine ligand exhibited high reactivity and stereocontrol in the desymmetrization of meso-epoxides with various alcohols. The respective enantiomerically enriched 1,2-alkoxyalcohols were obtained with e.r. values of up to 99.5:0.5 for various alcohols regardless of their nature (benzyl, alkyl, cycloalkyl, allyl, propargyl, etc.). We attempted ring-opening of meso-epoxides with anilines as well; however, it proceeded with lower enantioselectivity and was strongly depended on the electronic effect of substituents attached to the aromatic ring.
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