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- W2898157816 abstract "A novel cationic silicon–sulfur Lewis pair with a chiral H8-binaphthyl backbone is reported. It catalyzes otherwise sluggish Diels–Alder reactions of cyclohexa-1,3-diene and chalcone derivatives in good yields and decent enantioselectivities (up to 81% ee). The enantioinduction is highest with a [1,1′-biphenyl]-4-yl substituent at the carbonyl carbon atom. This moiety can be later converted into a carboxyl group by Baeyer–Villiger oxidation. The same oxidant also epoxidizes the double bond in the cycloadduct, and the epoxide engages in a lactonization with the carboxylic acid. Synthetically interesting hexahydro-3,6-methanobenzofuran-2(3H)-one skeletons are obtained in one pot." @default.
- W2898157816 created "2018-11-02" @default.
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- W2898157816 date "2018-10-26" @default.
- W2898157816 modified "2023-09-30" @default.
- W2898157816 title "Achieving Enantioselectivity in Difficult Cyclohexa-1,3-diene Diels–Alder Reactions with Sulfur-Stabilized Silicon Cations as Lewis Acid Catalysts" @default.
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- W2898157816 doi "https://doi.org/10.1021/acs.orglett.8b02945" @default.
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