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research article
Catalytic Enantioselective α-Ketol Rearrangement
A highly enantioselective a-ketol rearrangement has been developed. In the presence of a chiral Cu-bisoxazoline complex, achiral b-hydroxy-a-dicarbonyls were isomerized to chiral a-hydroxy-b-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.
Type
research article
Authors
Publication date
2019
Published in
Volume
58
Issue
2
Start page
499
End page
503
Peer reviewed
REVIEWED
EPFL units
Available on Infoscience
January 30, 2019
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