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 towards the (E) or (Z) isomer, useful precursors of 3(2’-amino)-beta-lactams.
G.Cardillo, S. Fabbroni, L. Gentilucci, R. Perciaccante, F. Piccinelli, A. Tolomelli (2005). Highly Diastereoselective Allylic Azide Formation and Isomerization. Synthesis of 3(2'-Amino)-beta-lactams. ORGANIC LETTERS, 7, 533-536 [10.1021/ol047815n].
Highly Diastereoselective Allylic Azide Formation and Isomerization. Synthesis of 3(2'-Amino)-beta-lactams
CARDILLO, GIULIANA;FABBRONI, SERENA;GENTILUCCI, LUCA;PERCIACCANTE, ROSSANA;PICCINELLI, FABIO;TOLOMELLI, ALESSANDRA
2005
Abstract
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 towards the (E) or (Z) isomer, useful precursors of 3(2’-amino)-beta-lactams.File in questo prodotto:
Eventuali allegati, non sono esposti
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
