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• W2125396281 abstract "An easy access to substituted (R)-3-hydroxy-3-phenyloxindoles, (R)-benzylic acids, and benzophenones is described. The reaction of the lithium enolate of the (2S,5S)-cis-1,3-dioxolan-4-one derived from optically active (S)-mandelic acid and pivalaldehyde with several o- and p-halonitrobenzenes proceeds readily to give the corresponding arylation products in good yields and diastereoselectivities. The reduction of the nitro group with Zn/HCl/EtOH in the o-nitro arylation products with concomitant intramolecular aminolysis of the dioxolanone moiety leads directly to enantiomerically pure (R)-3-hydroxy-3-phenyloxindoles. On the other hand the basic hydrolysis of the dioxolanone moiety in all the arylation products (ortho and para) leads to enantiomerically pure substituted (R)-benzylic acids. The oxidative decarboxylation of these latter with oxygen as terminal oxidant in the presence of pivalaldehyde and the Co(III)-Me2opba complex as catalyst gives substituted nitrobenzophenones." @default.
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• W2125396281 date "2004-09-03" @default.
• W2125396281 modified "2023-10-15" @default.
• W2125396281 title "Highly Diastereoselective Arylation of (<i>S</i>)-Mandelic Acid Enolate: Enantioselective Synthesis of Substituted (<i>R</i>)-3-Hydroxy-3-phenyloxindoles and (<i>R</i>)-Benzylic Acids and Synthesis of Nitrobenzophenones" @default.
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• W2125396281 doi "https://doi.org/10.1021/jo0402069" @default.
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