Amine-Promoted Synthesis of Vinyl Aziridines

N-Unsubstituted vinyl aziridines were synthesized via an amine-promoted regioselective nucleophilic aziridination of α,β,γ,δ-unsaturated carbonyl compounds. The reaction is completely regioselective (>95: 5) for the α,β-alkene and completely diastereoselective, affording the trans-vinyl aziridine...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 75; no. 10; pp. 3499 - 3502
Main Authors: Armstrong, Alan, Pullin, Robert D. C, Jenner, Chloe R, Scutt, James N
Format: Journal Article
Language:English
Published: Washington, DC American Chemical Society 21-05-2010
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Summary:N-Unsubstituted vinyl aziridines were synthesized via an amine-promoted regioselective nucleophilic aziridination of α,β,γ,δ-unsaturated carbonyl compounds. The reaction is completely regioselective (>95: 5) for the α,β-alkene and completely diastereoselective, affording the trans-vinyl aziridine in moderate-to-good yields.
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo100407s