Construction of Axial Chirality via Click Chemistry: Rh-Catalyzed Enantioselective Synthesis of 1-Triazolyl-2-Naphthylamines
Linwei Zeng, Fengzhi Zhang, Sunliang Cui
Abstract
A modular and practical click chemistry for atroposelective synthesis of 1-triazolyl-2-naphthylamines is developed. In this protocol, a variety of aromatic or aliphatic azides, and 1-alkynyl-2-naphthylamines could be assembled into valuable 1-triazlyl-2-naphthylamine scaffolds via a [3 + 2] cycloaddition under Rh-catalysis. This asymmetric click technology features easily accessible starting materials, mild reaction conditions, facile scalability, and good enantioselectivity. The good thermostability of products showcases great applicable potential, and the synthetic transformations further expand the molecular diversity of atropisomers.
Topics & Concepts
ChemistryEnantioselective synthesisClick chemistryCycloadditionCatalysisCombinatorial chemistryAtropisomerChirality (physics)ThermostabilityAxial chiralityOrganic chemistryPhysicsQuantum mechanicsQuarkEnzymeChiral symmetry breakingNambu–Jona-Lasinio modelClick Chemistry and ApplicationsAxial and Atropisomeric Chirality SynthesisChemical Synthesis and Analysis