Enantioselective synthesis of allenamides via sulfimide [2,3]-sigmatropic rearrangement.
Chiral allenamides are prepared with high levels of enantiomeric purity by [2,3]-sigmatropic rearrangement of propargylic sulfimides. The required branched propargylic sulfides are prepared by an enantioselective organocatalytic aldehyde alpha-sulfenylation followed by Corey-Fuchs alkynylation.
Armstrong
Alan
A
Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, UK.
Emmerson
Daniel P G
DP
D000447:Aldehydes / Q000737:chemistry; D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D013237:Stereoisomerism; D013440:Sulfides / Q000737:chemistry*
D000447:Aldehydes; D000466:Alkadienes; D000577:Amides; D013440:Sulfides; C025947:propadiene