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A Dual-Catalysis Approach to the Asymmetric Steglich Rearrangement and Catalytic Enantioselective Addition of O-Acylated Azlactones to Isoquinolines
journal contribution
posted on 2016-02-22, 18:57 authored by Chandra Kanta De, Nisha Mittal, Daniel SeidelA dual-catalysis approach, namely the combination of an achiral nucleophilic catalyst and a chiral anion-binding catalyst, was applied to the Steglich rearrangement to provide α,α-disubstituted amino acid derivatives in a highly enantioselective fashion. Replacement of the nucleophilic co-catalyst for isoquinoline resulted in a divergent reaction pathway and an unprecedented transformation of O-acylated azlactones. This strategy provided highly substituted α,β-diamino acid derivatives with excellent levels of stereocontrol.
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Steglich rearrangementenantioselective fashionApproachstereocontroldiaminoachiral nucleophilic catalystCatalytic Enantioselective AdditionstrategyAzlactoneReplacementapproachIsoquinolinesAcombinationisoquinolineazlactonetransformationdisubstitutedacid derivativesAsymmetric Steglich Rearrangementreaction pathway
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