Organocatalytic Higher-Order [8+2] Cycloaddition for the Assembly of Atropoenantiomeric 3-Arylindolizines
Gongming Yang, Zhipeng Li, Yuhan Liu, Donghui Guo, Xijun Sheng, Jian Wang
Abstract
We present an unprecedented atroposelective [8+2] cycloaddition reaction between pyridinium/isoquinolinium ylides and ynals. It is worth noting that this protocol represents a new example of the organocatalyzed atropoenantioselective higher-order cycloaddition reaction, providing various axial chiral 3-arylindolizines in good yields and high enantioselectivities. In addition, the obtained axially chiral 3-aryldolizines also provide many opportunities for structural transformations and potential drug discovery.
Topics & Concepts
CycloadditionChemistryPyridiniumCombinatorial chemistryOrganocatalysisAxial symmetryCatalysisAxial chiralityOrder (exchange)Computational chemistryOrganic chemistryEnantioselective synthesisMathematicsGeometryFinanceEconomicsSynthesis and Reactivity of HeterocyclesAxial and Atropisomeric Chirality SynthesisCyclopropane Reaction Mechanisms