Direct α-Benzylation of Methyl Enol Ethers with Activated Benzyl Alcohols: Its rearrangement and Access to (±)-Tetrahydronyasol, Propterol A and 1,3-Diarylpropane

Jena, Tapan Kumar and Khan, Faiz Ahmed (2019) Direct α-Benzylation of Methyl Enol Ethers with Activated Benzyl Alcohols: Its rearrangement and Access to (±)-Tetrahydronyasol, Propterol A and 1,3-Diarylpropane. The Journal of Organic Chemistry. ISSN 0022-3263

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Abstract

Herein we report a one-pot Lewis acid-mediated synthesis of bi, tri-arylpropanal derivative and their corresponding functional isomeric ketone derivatives from aromatic enol ethers. This transformation takes place via nucleophilic attack of enol ethers to electron rich benzyl alcohols (p-OMe). The substrate scope of this transformation indicates that the reaction might proceeds via quinomethoxy methide as a key intermediate which leads to propanal derivative and their Wagner-Meerwein rearrangement afforded isomeric ketones. Further, this methodology was applied for the synthesis of (±)-tetrahydronyasol, propterol A and 1,3-diarylpropane in short synthetic routes.

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