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Catalytic Asymmetric Synthesis of Vicinal Tetrasubstituted Diamines via Umpolung Cross-Mannich Reaction of Cyclic Ketimines.

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A catalytic asymmetric umpolung cross-Mannich reaction of cyclic ketimines is realized. This protocol provides an efficient methodology for the facile synthesis of chiral vicinal tetrasubstituted diamines in high yields with… Click to show full abstract

A catalytic asymmetric umpolung cross-Mannich reaction of cyclic ketimines is realized. This protocol provides an efficient methodology for the facile synthesis of chiral vicinal tetrasubstituted diamines in high yields with excellent chemo-, regio-, diastereo-, and enantioselectivities using cinchona-derived bifunctional organocatalysts (85-98% yield, up to >20:1 dr, and >99% ee).

Keywords: mannich reaction; reaction cyclic; cyclic ketimines; umpolung cross; catalytic asymmetric; cross mannich

Journal Title: Organic letters
Year Published: 2020

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