We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
One-Pot Three-Component Synthesis of Vicinal Diamines via In Situ Aminal Formation and Carboamination.
- Authors
Orcel, Ugo; Waser, Jerome
- Abstract
A synthesis of vicinal diamines via in situ aminal formation and carboamination of allyl amines is reported. Employing highly electron-poor trifluoromethyl aldimines in their stable hemiaminal form was key to enable both a fast and complete aminal formation as well as the palladium-catalyzed carboamination step. The conditions developed allow the introduction of a wide variety of alkynyl, vinyl, aryl, and hetereoaryl groups with complete regioselectivity and high diastereoselectivity. The reaction exhibits a high functional-group tolerance. Importantly, either nitrogen atom of the imidazolidine products can be selectively deprotected, while removal of the aminal tether can be achieved in a single step under mild conditions to reveal the free diamine. We expect that this work will promote the further use of mixed aminal tethers in organic synthesis.
- Subjects
DIAMINES; AMINATION; ALLYLAMINES; PALLADIUM catalysts; REGIOSELECTIVITY (Chemistry); IMIDAZOLIDINES; ALDIMINES; TRIFLUOROMETHYL compounds
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 41, p13073
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201607318