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Intramolecular Umpolung Allylation of Imines.

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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… Click to show full abstract

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.

Keywords: intramolecular umpolung; umpolung allylation; allylation imines

Journal Title: Organic letters
Year Published: 2018

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