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A Mn(III)-catalysed domino process for C-3 substituted dihydrocoumarins from 2-hydroxybenzyl alcohols and
Gokul S Londhe1, Shankhajit Mondal1, Boopathy Gnanaprakasam1
1Department of Chemistry, Indian Institute of Science Education and Research Dr Homi Bhabha Road, Pashan, Pune-411008, India. gnanaprakasam@iiserpune.ac.in.
Abstract:
A Mn-catalysed efficient domino process for the synthesis of new C-3 substituted dihydrocoumarins from 2-hydroxybenzyl alcohols and 4-hydroxy-2H-chromen-2-ones under one-pot conditions is described. This reaction proceeds via a series of reactions in one-pot, such as o-quinone methide formation, Michael addition, intramolecular transesterification, and skeletal rearrangement to access dihydrocoumarins.
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The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.