Photochemical rearrangement of N-mesyloxylactams: stereospecific formation of N-heterocycles.
N-Mesyloxylactams undergo an efficient ring-contraction to N-heterocycles of various ring sizes. Yields increase with the degree of substitution α to the carbonyl. The stereochemical information of a chiral migrating carbon is conserved making this reaction a synthetically useful complement to the well-known Hofmann, Curtius, Lossen, and Schmidt rearrangements.
Département de Chimie, Université de Sherbrooke, 2500 boul. Université, Sherbrooke, Québec, Canada, J1K 2R1.
Alexandre
A
Drouin
Dana K
DK
Winter
Simon
S
Pichette
Samuel
S
Aubert-Nicol
Jean
J
Lessard
Claude
C
Spino
D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D055668:Photochemical Processes; D013237:Stereoisomerism
D006571:Heterocyclic Compounds; D007769:Lactams; D008698:Mesylates