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Back Cover: Water Structure Recovery in Chaotropic Anion Recognition: High-Affinity Binding of Dodecaborate Clusters to γ-Cyclodextrin (Angew. Chem. …

2015

γ cyclodextrinChaotropic agentHofmeister seriesHigh affinity bindingChemistryINTInorganic chemistryDodecaborateSupramolecular chemistryGeneral ChemistryMedicinal chemistryCatalysisIonAngewandte Chemie International Edition
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Desymmetrization of Prochiral Cyclobutanones via Nitrogen Insertion: A Concise Route to Chiral γ‐Lactams

2021

Abstract Asymmetric access to γ‐lactams is achieved via a cyclobutanone ring expansion using widely available (1S,2R)‐1‐amino‐2‐indanol for chiral induction. Mechanistic analysis of the key N,O‐ketal rearrangement reveals a Curtin–Hammett scenario, which enables a downstream stereoinduction (up to 88:12 dr) and is corroborated by spectroscopic, crystallographic, and computational studies. In combination with an easy deprotection protocol, this operationally simple sequence allows the synthesis of a range of optically pure γ‐lactams, including those bearing all‐carbon quaternary stereocenters. In addition, the formal synthesis of drug molecules baclofen, brivaracetam, and pregabalin further …

γ-lactamsChiral auxiliary010405 organic chemistryChemistryasymmetric synthesisEnantioselective synthesisCyclobutanoneGeneral Chemistry010402 general chemistryRing (chemistry)01 natural sciencesCombinatorial chemistryDesymmetrizationCatalysis0104 chemical sciencesStereocenterdesymmetrizationFormal synthesischemistry.chemical_compoundMoleculecyclobutanoneResearch ArticlesResearch ArticleAsymmetric Synthesis | Hot PaperAngewandte Chemie International Edition
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