Nickel‐Catalyzed Enantioselective Reductive Amination of Ketones with Both Arylamines and Benzhydrazide. (30th August 2016)

• Record Type: Journal Article
• Authors: Yang, Peng; Lim, Li Hui; Chuanprasit, Pratanphorn; Hirao, Hajime; Zhou, Jianrong (Steve)
• Is Part Of: Angewandte Chemie. Volume 128:Number 39(2016)
• Page Start: 12262
• Page End: 12266
• Publication Date: 2016-08-30
• Subjects: Chirale Alkylamine -- Nickel -- Reduktive Aminierungen -- Synthesemethoden -- Transferhydrierungen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201606821
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: An asymmetric reductive amination of ketones using both arylamines and benzhydrazide in the presence of nickel catalysts was developed. A one‐pot synthesis of tetrahydroquinoxalines was also developed starting directly from α‐ketoaldehydes and 1, 2‐diaminobenzene. Formic acid was used as a safe and economic surrogate for high‐pressure hydrogen gas. Strongly σ‐donating bis(alkylphosphine)s are crucial ancillary ligands for both stereoselective hydride insertion and decarboxylation of the formate.