Amine-promoted synthesis of vinyl aziridines.
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.
Armstrong
Alan
A
Department of Chemistry, Imperial College London, South Kensington, London, SW7 2AZ, United Kingdom. a.armstrong@imperial.ac.uk
Pullin
Robert D C
RD
Jenner
Chloe R
CR
Scutt
James N
JN
D000588:Amines / Q000737:chemistry*; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000588:Amines; D001388:Aziridines