Nickel-Catalyzed Decarboxylative Generation and Asymmetric Allylation of 2-Azaallyl Anions

• DOI: 10.1021/acs.joc.9b01293
• Publication Date: 2019-07-22T14:47:34Z
• Authors: Chenlu Liu; Changfeng Deng; Han Yang; Xiaoyan Qian; Shaojian Tang; Michal Poznik; Jason J. Chruma
• Keywords: Decarboxylation; Enantiomeric excess

The first nickel-catalyzed asymmetric decarboxylative allylation (DcA) of allyl 2,2-diarylglycinate imines is reported. This transformation utilizes a chiral ferrocenyl bidentate ligand and Ni(0) precatalyst to mediate the generation 2-azaallyl anions, affording α-aryl homoallylic in modest-to-high yields moderate-to-high enantiomeric ratios. resulting Ni-catalyzed proved be less general comparison our previously reported analogous Pd-mediated protocol, but it still exhibited certain advantages regard regio- enantioselectivity C–C bond formation.