Catalytic Enantioselective α‐Ketol Rearrangement |
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Authors: | Hua Wu,R mi Andres,Qian Wang,Jieping Zhu |
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Affiliation: | Hua Wu,Rémi Andres,Qian Wang,Jieping Zhu |
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Abstract: | A highly enantioselective α‐ketol rearrangement has been developed. In the presence of a chiral Cu‐bisoxazoline complex, achiral β‐hydroxy‐α‐dicarbonyls were isomerized to chiral α‐hydroxy‐β‐dicarbonyls and their bicyclic derivatives in excellent yields and enantioselectivities. Enantioenriched 2‐acyl‐2‐hydroxy cyclohexan‐1‐ones, dihydroxyhexahydrobenzofuranones, and dihydroxyhexahydro‐cycloheptafuranones, with up to three stereocenters, were readily prepared from achiral starting materials in one operation. The reaction is applicable to the desymmetrization of meso substrates and kinetic resolution of racemic alcohols. |
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Keywords: | Asymmetrische Synthesen Desymmetrisierung Kinetische Racematspaltung Kupfer Umlagerungen |
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