Atroposelective Synthesis of 1,1′‐Bipyrroles Bearing a Chiral N−N Axis: Chiral Phosphoric Acid Catalysis with Lewis Acid Induced Enantiodivergence
Yaru Gao, Luo‐Yu Wang, Tao Zhang, Bin‐Miao Yang, Yu Zhao
Abstract
Abstract We present herein a highly efficient atroposelective synthesis of axially chiral 1,1′‐bipyrroles bearing an N−N linkage from simple hydrazine and 1,4‐diones. Further product derivatizations led to axially chiral bifunctional compounds with high potential in asymmetric catalysis. For this chrial phosphoric acid (CPA)‐catalyzed double Paal–Knorr reaction, an intriguing Fe(OTf) 3 ‐induced enantiodivergence was also observed.
Topics & Concepts
ChemistryPhosphoric acidCatalysisLewis acids and basesBifunctionalAxial chiralityAcid catalysisEnantioselective synthesisCombinatorial chemistryLewis acid catalysisOrganic chemistryStereochemistryMedicinal chemistryAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralitySphingolipid Metabolism and Signaling