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- W2028863148 endingPage "4654" @default.
- W2028863148 startingPage "4643" @default.
- W2028863148 abstract "A strategy based on diastereoselective epoxidation of a cyclohexene followed by chiral lithium amide-mediated epoxide rearrangement has been used to synthesise an allylic alcohol building block of >95% ee. The key step is the enantioselective rearrangement of a bis-protected meso-4,5-dihydroxycyclohexene oxide. A range of protecting groups and chiral base structures were surveyed in order to find the optimum protocol for high enantioselectivity. Using a tert-butyldimethylsilyloxy protecting group and a norephedrine-derived chiral base, a 93% yield of an allylic alcohol of >95% ee was achieved. To demonstrate the synthetic utility, this allylic alcohol was subsequently transformed into 4-deoxyconduritols and (+)-conduritol F." @default.
- W2028863148 created "2016-06-24" @default.
- W2028863148 creator A5002767417 @default.
- W2028863148 creator A5074030394 @default.
- W2028863148 creator A5076219690 @default.
- W2028863148 date "2002-06-01" @default.
- W2028863148 modified "2023-10-09" @default.
- W2028863148 title "Optimisation of enantioselectivity for the chiral base-mediated rearrangement of bis-protected meso-4,5-dihydroxycyclohexene oxides: asymmetric synthesis of 4-deoxyconduritols and conduritol F" @default.
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- W2028863148 doi "https://doi.org/10.1016/s0040-4020(02)00370-8" @default.
- W2028863148 hasPublicationYear "2002" @default.
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