A Central-to-Axial Chirality Conversion Strategy for the Synthesis of C–N Axially Chiral <i>N</i>-Arylpyrroles
Yuan Zhao, Ningning Liu, Shiping Zhong, Ziwei Wen, Tao Wang
Abstract
We present a central-to-axial chirality conversion strategy for the construction of C–N axially chiral N-arylpyrroles via a gold(I)-catalyzed 5-endo-dig cyclization/dehydration cascade from amino acid derivatives. The reaction exhibits high efficiency on the central-to-axial chirality conversion. Density functional theory calculations suggest that the stereospecificity during the central-to-axial chirality conversion lies in the stability of the conformations of the amino alcohol and the corresponding low barrier transition state.
Topics & Concepts
Chirality (physics)Axial symmetryAxial chiralityChemistryCascadeStereospecificityStereochemistryComputational chemistryCatalysisPhysicsOrganic chemistryEnantioselective synthesisQuantum mechanicsChiral symmetry breakingSymmetry breakingNambu–Jona-Lasinio modelChromatographyAxial and Atropisomeric Chirality SynthesisTraditional and Medicinal Uses of AnnonaceaeAsymmetric Synthesis and Catalysis