Lewis acid-catalyzed [3+3] cycloadditions of donor‒acceptor aziridines with N,N-dialkyl-3-vinylanilines via carbon-carbon bond cleavage

Add time:08/24/2019    Source:sciencedirect.com

A Lewis acid-catalyzed [3 + 3] cycloaddition reaction of donor‒acceptor aziridines with N,N-dialkyl-3-vinylanilines has been developed for the stereoselective synthesis of tetrahydroisoquinolines (THIQs). The reaction performed using Gd(OTf)3 as the Lewis acid catalyst was tolerant to various N-tosylaziridine and N,N-dialkyl-3-vinylaniline substrates and provided access to highly functionalized THIQs in typically high yields with moderate-to-excellent diastereoselectivities.

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