Stereo-controlled enolboration-aldolization of esters such as acetates, propionates, 3,3,3-trifluoropropionates, and phenylacetates are well investigated. However, those reactions of carboxylic acid amides are rarely reported. We have used dialkylboron triflate (R2BOTf) in the presence of a trialkyl amine (R3N) to enolize N,N-dialkylphenylacetamide followed by aldolization with various aldehydes. We have also studied the effects of various factors such as bulk of a boron reagent, solvent used, reaction temperature, and steric of alkyl groups of tertiary amides to optimize both syn- as well as anti-selective reaction conditions. We will present the reaction optimization strategies and the scope of both syn- and anti-selective enolboration-aldolization of N,N-dialkylphenylacetamides.

Diastereoselective enolboration-aldolization of N,N-dialkylphenylacetamides

ACS Spring Meeting 2021

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