The stereoselective anti S(N)2' 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.

Highly diastereoselective allylic azide formation and isomerization. Synthesis of 3(2 '-amino)-beta-lactams

PICCINELLI, FABIO;
2005

Abstract

The stereoselective anti S(N)2' 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.
ALPHA; BETA-UNSATURATED ACID-CHLORIDES; O-H INSERTION; BETA-LACTAMS
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11562/736019
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