Palladium/Xu-Phos-catalyzed asymmetric carboamination towards isoxazolidines and pyrrolidines

Chem Sci. 2021 May 5;12(23):8241-8245. doi: 10.1039/d1sc01337h.

Abstract

An efficient palladium-catalyzed enantioselective carboamination reaction of N-Boc-O-homoallyl-hydroxylamines and N-Boc-pent-4-enylamines with aryl or alkenyl bromides was developed, delivering various substituted isoxazolidines and pyrrolidines in good yields with up to 97% ee. The reaction features mild conditions, general substrate scope and scalability. The obtained products can be transformed into chiral 1,3-aminoalcohol derivatives without erosion of chirality. The newly identified Xu-Phos ligand bearing an ortho-OiPr group is responsible for the good yield and high enantioselectivity.