Synthesis of Axially Chiral <i>N</i>-Arylpyrroles through the Enantioselective Annulation of Yne-Allylic Esters with a Cooperative Copper-Squaramide Catalysis
Maoyan Liao, Jixing Li, Haihui Zhu, Zhengyu Han, Yuzhe Zhang, Jianwei Sun, Hai Huang
Abstract
We present a strategy involving central-to-axial chirality conversion for the construction of axially chiral N -arylpyrroles via a cooperative copper-squaramide-catalyzed remote propargylic amination/ring closure/rearomatization cascade from yne-allylic esters. The reaction exhibits excellent chemical efficiency and enantioselectivity, involving good central-to-axial chirality conversion. The use of squaramide as cocatalyst is crucial for the success.
Topics & Concepts
SquaramideChemistryEnantioselective synthesisAnnulationAllylic rearrangementCatalysisCopperCombinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryOrganocatalysisAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityAsymmetric Synthesis and Catalysis