Asymmetric Aminocatalysis in the Synthesis of delta-Lactone Derivatives

作者:Albrecht Anna; Skrzynska Anna; Pietrzak Anna; Bojanowski Jan; Albrecht Lukasz*
来源:Asian Journal of Organic Chemistry, 2016, 5(9): 1115-1119.
DOI:10.1002/ajoc.201600272

摘要

In this manuscript, a novel approach to 3,4-dihydrocoumarins is presented. It utilizes the aminocatalytic, trienamine-mediated cycloaddition reaction between 2,4-dienals and ethyl coumarincarboxylates. The reaction is promoted by a bifunctional aminocatalyst bearing a hydrogen-bonding squaramide structural unit. As a consequence, the stereochemical outcome is governed through the double hydrogen-bonding interactions between the hydrogen-bonding moiety of the catalyst and the dienophile. The transformation of the obtained cycloadducts into 3,4-dihydrocoumarins bearing a bislactone structural motif is presented.

  • 出版日期2016-9