β-Cyclodextrin-NHC-Au(I)-Catalyzed Enantioconvergent 1,5-enyne Cycloisomerizations - Sorbonne Université
Journal Articles Organic Letters Year : 2024

β-Cyclodextrin-NHC-Au(I)-Catalyzed Enantioconvergent 1,5-enyne Cycloisomerizations

Abstract

Enantioconvergent transformations from racemic mixtures are attractive since they allow to generate optically active products with full conversion despite the possibly adverse kinetic resolution process. When dealing with gold(I)-catalyzed cycloisomerizations, chirality transfer from the precursor is another possible diverting pathway, which renders enantioconvergence challenging. Not surprisingly, enantioconvergent Au(I)-catalyzed processes have re- mained extremely rare. Herein, we show that cavity-driven catalysis using β-Cyclodextrin-NHC-Au(I) complexes bring opportunities to conduct highly enantioconvergent cycloisomerizations of 1,5-enynes, -enynols and –enynyl esters.
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Dates and versions

hal-04644245 , version 1 (10-07-2024)

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Mehdi Koohgard, Lukas Enders, Natalia del Rio, Hang Li, Fabio Moccia, et al.. β-Cyclodextrin-NHC-Au(I)-Catalyzed Enantioconvergent 1,5-enyne Cycloisomerizations. Organic Letters, In press, ⟨10.1021/acs.orglett.4c02003⟩. ⟨hal-04644245⟩
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