Organocatalytic Remote Stereocontrolled Synthesis of Tetrasubstituted Allenes via Asymmetric 1,8‐Addition of Propargylic Aza‐<i>p</i>‐Quinone Methides
Zhibin Yue, Yan Xia, Boming Shen, Chang Liu, Peiyuan Yu, Pengfei Li, Wenjun Li
Abstract
Abstract An organocatalytic remote stereocontrolled 1,8‐conjugated addition of in situ formed propargylic aza‐ p ‐QMs from α‐(4‐aminophenyl) propargylic alcohols and indole‐2‐carboxylates was developed, affording axially chiral tetrasubstituted allenes in 62–99% yield with 52–99% ee. The synthetic strategy not only enriches the chemistry of aza‐ p ‐quinone methides, but also provides an alternative tool for the preparation of axially chiral tetrasubstituted allenes.
Topics & Concepts
ChemistryYield (engineering)Enantioselective synthesisQuinoneConjugated systemCombinatorial chemistryOrganocatalysisIndole testOrganic chemistryStereochemistryCatalysisPolymerMetallurgyMaterials scienceSynthesis of Indole DerivativesAxial and Atropisomeric Chirality SynthesisAlkaloids: synthesis and pharmacology