Nickel-Catalyzed Enantioselective Direct Addition of Styrenes to Imines Enabled by Chiral Spiro Phosphine Ligands
Yewei Huang, Tianze Zhang, Shihui Cheng, Qi‐Lin Zhou, Li‐Jun Xiao
Abstract
Enantioenriched allylic amines are key structural motifs found in a wide array of bioactive molecules and serve as versatile intermediates in organic synthesis. Despite significant advances in their preparation, the enantioselective direct addition of simple alkenes to imines has remained a formidable challenge. Herein, we report a nickel(0)-catalyzed enantioselective direct addition of styrenes and their derivatives to aldimines, enabled by a newly developed family of electron-rich, C 2 -symmetric chiral spiro monophosphine ligands based on the tetramethyl-1,1′-spirobiindane scaffold. This method features highly efficient, atom-economical construction of chiral allylic amines with excellent regio- and enantioselectivities under mild conditions, and exhibits broad functional group tolerance.