Due to the wide range of biological activities of polysubstituted furans, several synthetic techniques have been devised. This review article describes the most recent developments in the synthesis of polysubstituted furans using transition-metal...
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Three‐Component Aza‐Diels‐Alder Reaction for the Syntheses of Tetrahydroisoquinoline Derivatives
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A series of tetrahydroisoquinoline derivatives were prepared via a three-component aza-Diels-Alder reaction. Keys to the success of this reaction are a) the utilization of sultines as masked o-quinodimethanes, b) the facile, in situ generation of imine dienophiles, and c) the presence of Cu(OTf)2 as a Lewis acid to promote the desired reactivity.
Abstract
Reported herein is the development of a normal electron-demand, three-component aza-Diels-Alder reaction between sultines, aldehydes, and amines. In the presence of Cu(OTf)2 as a Lewis acid catalyst, the use of sultines as o-quinodimethane precursors in conjunction with the in situ generation of imines enables the facile preparation of various polysubstituted tetrahydro-isoquinoline derivatives from readily available substrates. The synthetic utility of these products was further explored through a number of product transformations, including the syntheses of tricyclic N-heterocycles.
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