Tandem Insertion–[1,3]‐Rearrangement: Highly Enantioselective Construction of α‐Aminoketones
Yushuang Chen, Yun Liu, Zhaojing Li, Shunxi Dong, Xiaohua Liu, Xiaoming Feng
Abstract
Abstract An enantioselective synthesis of α‐aminoketone derivatives were readily available through a tandem insertion–[1,3] O‐to‐C rearrangement reaction. The rhodium salt and chiral N , N ′‐dioxide‐indium(III) complex make up relay catalysis, which enables the O−H insertion of benzylic alcohols to N ‐sulfonyl‐1,2,3‐triazoles, and asymmetric [1,3]‐rearrangement of amino enol ether intermediates, subsequently. Preliminary mechanistic studies suggested that the [1,3] O‐to‐C rearrangement step proceeded through an ion pair pathway.
Topics & Concepts
Enantioselective synthesisChemistrySulfoniumRhodiumRearrangement reactionTandemStereochemistryCatalysisCope rearrangementCarroll rearrangementEtherMigratory insertionCombinatorial chemistryMedicinal chemistrySalt (chemistry)Claisen rearrangementOrganic chemistryMaterials scienceComposite materialSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and CatalysisCyclopropane Reaction Mechanisms