Control of chemoselectivity in asymmetric tandem reactions: Direct synthesis of chiral amines bearing nonadjacent stereocenters

• DOI: 10.1073/pnas.1718474115
• Publication Date: 2018-02-05T20:20:35Z
• Authors: Zhe Li; Bin Hu; Yongwei Wu; Chao Fei; Li Deng
• Keywords: Molecular Structure; Phenol; Stereoisomerism; Imines; Amines; 01 natural sciences; Catalysis; 0104 chemical sciences

This paper describes the mechanistic insight-guided development of a catalyst system, employing a phenolic proton donor catalyst in addition to a cinchonium-derived phase-transfer catalyst, to control the chemoselectivity of two distinct intermediates, thereby enabling the desired asymmetric tandem conjugate addition–protonation pathway to dominate over a number of side-reaction pathways to provide a synthetic approach for the direct generation of optically active amines bearing two nonadjacent stereocenters.