Enantioselective Organocatalytic Allylic Amination
- 2 August 2005
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (33) , 11614-11615
- https://doi.org/10.1021/ja0539847
Abstract
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.Keywords
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