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Enantioselective Organocatalytic Allylic Amination

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journal contribution
posted on 24.08.2005, 00:00 authored by Thomas B. Poulsen, Carlos Alemparte, Karl Anker Jørgensen
A new strategy for catalytic enantioselective allylic amination based on organocatalysis has been developed. Using a commercially available organocatalyst we demonstrate a direct highly enantioselective allylic electrophilic functionalization of alkylidene cyanoacetates and malononitriles with azodicarboxylates. The reaction is broad in scope and proceeds in high yields and with enantioselectivities up to 99%. Furthermore, we demonstrate the synthetic utility of the optically active products formed:  highly diastereoselective Diels−Alder reaction, reduction, and formation of optically active building blocks, which are found in various important bioactive compounds such as quinacrine, chloroquine, and analogues thereof.