Synthesis of Axially Chiral CF<sub>3</sub>‐Substituted 2‐Arylpyrroles by Sequential Phosphine‐Catalyzed Asymmetric [3+2] Annulation and Oxidative Central‐to‐Axial Chirality Transfer
Chuan Xiang Alvin Tan, Rui Li, Fuhao Zhang, Lei Dai, Nisar Ullah, Yixin Lü
Abstract
Abstract A sequential phosphine‐catalyzed asymmetric [3+2] annulation of aldimines with allenoates and oxidative central‐to‐axial chirality transfer strategy has been developed. This approach is operationally simple, allowing for rapid access to a range of axially chiral CF 3 ‐containing 2‐arylpyrroles with high enantiomeric excess. Furthermore, an atroposelective synthesis of esaxerenone is presented, illustrating the practical potential of the reported method.
Topics & Concepts
Axial chiralityAnnulationChirality (physics)EnantiomerPhosphineAxial symmetryAldimineChemistryCatalysisEnantioselective synthesisOxidative phosphorylationCombinatorial chemistryStereochemistryOrganic chemistryPhysicsChiral symmetryQuantum mechanicsBiochemistryQuarkNambu–Jona-Lasinio modelAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityAlgebraic structures and combinatorial models