Asymmetric synthesis of atropisomeric arylpyrazoles <i>via</i> direct arylation of 5-aminopyrazoles with naphthoquinones
Jiamin Liu, Xingfu Wei, Yue Wang, Jingping Qü, Baomin Wang
Abstract
Construction of axially chiral arylpyrazoles represents an attractive challenge due to the relatively low rotational barrier of biaryl structures containing five-membered heterocycles. This work describes the catalytic asymmetric construction of axially chiral arylpyrazoles using 5-aminopyrazoles and naphthoquinone derivatives. The chiral axis could be formed through a central-to-axial chirality relay step of the chiral phosphoric acid-catalyzed arylation reaction, which features excellent yields and enantioselectivities with a broad substrate scope under mild reaction conditions.
Topics & Concepts
Chirality (physics)ChemistryAtropisomerCombinatorial chemistryStereochemistryPhysicsParticle physicsQuarkNambu–Jona-Lasinio modelChiral symmetry breakingAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityChemical synthesis and alkaloids