Organocatalytic Asymmetric [4 + 2] Cyclization of Azadienes with Azlactones: Access to Chiral 3-Amino-δ-Lactams Derivatives
Wu-Jingyun Zhou, Xiaoning Yu, Chen Chen, Wei Lan, Gu Zhan, Jin Zhou, Qian Liu, Wei Huang, Qian‐Qian Yang
Abstract
Herein, a series of chiral δ-lactam frameworks have been synthesized and catalyzed by chiral phosphoric acid (CPA) utilizing two kinds of open-chain aza-dienes and azlactones derived from amino acids. This powerful [4 + 2] annulation produces a broad substrate scope with functional group tolerance in yield up to 97% with up to 98:2 er. Moreover, a facile scale-up and straightforward conversion to diversely substituted products verify the synthetic utility of this method featuring good compatibility and high efficiency.
Topics & Concepts
Phosphoric acidChemistryAnnulationCombinatorial chemistryEnantioselective synthesisSubstrate (aquarium)Functional groupYield (engineering)Scope (computer science)Compatibility (geochemistry)OrganocatalysisStereochemistryCatalysisOrganic chemistryComputer scienceMaterials scienceBiologyMetallurgyPolymerEcologyComposite materialProgramming languageSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsAsymmetric Synthesis and Catalysis