Towards Axially Chiral Pyrazole‐Based Phosphorus Scaffolds by Dipeptide‐Phosphonium Salt Catalysis
Jia‐Hong Wu, Jian‐Ping Tan, Jia‐Yan Zheng, Jiajia He, Zhenlei Song, Zhishan Su, Tianli Wang
Abstract
Given the comparatively lower rotational barriers, the catalytic asymmetric construction of axially chiral biaryl structures, especially those containing a five-membered heterocycle, still remains a challenge. Herein, we described a general and modular protocol to access atropisomeric arylpyrazole scaffolds containing a phosphorus unit by a dipeptide phosphonium salt catalyzed reaction involving an oxidative central-to-axial chirality conversion. This reaction features excellent yields and enantioselectivities, broad substrate scope, and a low catalyst loading, delivering axially chiral phosphine compounds.
Topics & Concepts
PhosphoniumAxial chiralityCatalysisDipeptideChirality (physics)ChemistryAxial symmetryPhosphonium saltSalt (chemistry)Combinatorial chemistryPhosphineEnantioselective synthesisSubstrate (aquarium)EnantiomerPyrazoleOrganic chemistryAmino acidChiral symmetry breakingPhysicsSymmetry breakingBiochemistryGeologyQuantum mechanicsOceanographyNambu–Jona-Lasinio modelAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityAlgebraic structures and combinatorial models