Rearrangement of β,γ-Unsaturated Esters with Thallium Trinitrate: Synthesis of Indans Bearing a β-Keto Ester Moiety
نویسندگان
چکیده
The indan skeleton is present in a variety of molecules with important biological activity, including the wellknown Indinavir and Aricept. Our research group has investigated approaches to obtain indans from 1,2dihydronaphthalenes, using a thallium(III)-promoted ring contraction reaction. During these studies, we found that a side chain at the double bond has a strong influence in the reaction pathway. The treatment of 1,2-dihydronaphthalenes bearing a β,γ-unsaturated carboxylic acid unit, such as 1, with thallium triacetate (TTA) gave a mixture of the isomeric allylic acetates 2 and 3, which are produced through an oxidative decarboxylation process (Scheme 1).
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