Abstract
AbstractStereodivergent synthesis of N-heterocycle frameworks bearing 1,3-nonadjacent stereogenic centers through a single transformation remains a high-priority challenge in organic synthesis. Herein, we highlight our recent discovery of stereodivergent access to such useful structural motifs using Pd-catalyzed [4+2] annulation reactions of vinyl benzoxazinaones and seven-membered cyclic N-sulfonyl aldimines. A wide range of N-heterocycles with 1,3-nonadjacent stereogenic centers were obtained in high efficiency and stereodivergency. Importantly, the polarity of solvents was found to play a key role in switching the diastereoselectivity. Furthermore, good enantioselectivities of these reactions were achieved by the employment of commercially available Wingphos as the chiral ligand.
Funder
National Natural Science Foundation of China
Xi’an Jiaotong University