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We report an approach to the diastereoselective synthesis of 1,2-disubstituted heterocyclic aziridines. A Brønsted acid-catalyzed conjugate addition of anilines to trisubstituted heterocyclic chloroalkenes provides an intermediate 1,2-chloroamine. Diastereocontrol was found to vary significantly with solvent selection, with computational modelling confirming selective, spontaneous fragmentation in the presence of trace acids, proceeding through a pseudo-cyclic, protonated intermediate and transition state. These chloroamines can then be converted to the aziridine by treatment with LiHMDS with high stereochemical fidelity. This solvent-induced stereochemical enrichment thereby enables an efficient route to rare cis-aziridines with high dr. The scope, limitations, and mechanistic origins of selectivity are also presented
FingerprintDive into the research topics of 'Accessing rare α-heterocyclic aziridines via Brønsted acid-catalyzed Michael addition/annulation: scope, limitations, and mechanism'. Together they form a unique fingerprint.
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Dataset underpinning "Accessing Rare α-Heterocyclic Aziridines via Brønsted Acid- catalyzed Michael Addition/Annulation: Scope, Limitations, and Mechanism"
Watson, A. J. B. (Creator), University of St Andrews, 16 Nov 2023