One‐Pot Three‐Component Synthesis of Vicinal Diamines via In Situ Aminal Formation and Carboamination. (16th September 2016)

• Record Type: Journal Article
• Authors: Orcel, Ugo; Waser, Jerome
• Is Part Of: Angewandte Chemie. Volume 128:Number 41(2016)
• Page Start: 13073
• Page End: 13077
• Publication Date: 2016-09-16
• Subjects: Alkene -- Aminale -- Homogene Katalyse -- Pd-Katalyse -- Vicinale Diamine; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201607318
• Languages: English
• ISSNs: 0044-8249

Abstract

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.