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Intramolecular Umpolung Allylation of Imines

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journal contribution
posted on 11.09.2018 by Miao Zhan, Xiang Pu, Bin He, Dawen Niu, Xia Zhang
An intramolecular umpolung allylation of imines is reported. This reaction occurs via the intermediacy of 2-azaallyl anions. It could proceed either under transition-metal-catalyzed conditions or under transition-metal-free conditions. Importantly, this approach afforded trans-3-vinyl-4-aminochromanes with high diastereoselectivity, while conventional, nonumpolung methods often display high cis-selectivity.