Intramolecular Umpolung Allylation of Imines

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