Abstract
Abstract 1-Mesitylethylamine was designed as a new non-natural chiral auxiliary. Racemic 1-mesitylethylamine could be synthesized in two steps from mesityl cyanide and could be resolved via separation of diastereomeric carbamates derived from (−)-menthyl chloroformate, followed by reduction with DIBAL and acidic hydrolysis. Imines, prepared from enantiopure 1-mesitylethylamine and aromatic aldehydes, reacted with Danishefsky’s diene in the presence of a Lewis acid to give cycloaddition products, 4-pyridone derivatives, with high diastereoselectivity.
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