Highly diastereoselective allylic azide formation and isomerization. Synthesis of 3(2'-amino)-beta-lactams.
The stereoselective anti SN2' attack of NaN3 to 3-alkenyl-3-bromo-azetidin-2-ones gave a mixture of diastereomeric azides in fast equilibrium. The [3,3]-sigmatropic rearrangement of allylic azides occurred with complete stereocontrol, allowing the equilibrium to be directed preferentially toward the (E)- or (Z)-isomer, useful precursors of 3(2'-amino)-beta-lactams. [reaction: see text]
Cardillo
Giuliana
G
Department of Chemistry G. Ciamician, University of Bologna, Via Selmi 2, 40126 Bologna, Italy. giuliana.cardillo@unibo.it
Fabbroni
Serena
S
Gentilucci
Luca
L
Perciaccante
Rossana
R
Piccinelli
Fabio
F
Tolomelli
Alessandra
A
D000498:Allyl Compounds / Q000138:chemical synthesis*; D000588:Amines / Q000138:chemical synthesis; D007536:Isomerism; D008958:Models, Molecular; D008968:Molecular Conformation; D010087:Oxides / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014961:X-Ray Diffraction; D047090:beta-Lactams / Q000138:chemical synthesis*
D000498:Allyl Compounds; D000588:Amines; D010087:Oxides; D047090:beta-Lactams