N-Unsubstituted vinyl aziridines were synthesized via an amine-promoted regioselective nucleophilic aziridination of alpha,beta,gamma,delta-unsaturated carbonyl compounds. The reaction is completely regioselective (>95: 5) for the alpha,beta-alkene and completely diastereoselective, affording the trans-vinyl aziridine in moderate-to-good yields.
Cinchona alkaloid-catalyzed reaction of ethyl glyoxylate with substituted ketenes, formed in situ, gives disubstituted beta-lactones in moderate yield and high enantiomeric excess. Subsequent azide ring opening, reduction, and ester hydrolysis allows access to chiral beta-alkyl aspartates.
Tertiary Amine-Promoted Enone Aziridination: Investigations into Factors Influencing Enantioselective Induction. -Upon several tested tertiary amines quinine shows to be the best promoter for the asymmetric aziridination of ,-unsaturated ketones. The reaction proceeds via N-aminoquininium salts. -(ARMSTRONG*, A.; PULLIN, R. D. C.; JENNER, C. R.; FOO, K.; WHITE, A. J. P.; SCUTT, J. N.; Tetrahedron: Asymmetry 25 (2014) 1, 74-86, http://dx.
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