Highly diastereoselective allylic azide formation and isomerization. Synthesis of 3(2'-amino)-beta-lactams |
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| Authors: | Cardillo Giuliana Fabbroni Serena Gentilucci Luca Perciaccante Rossana Piccinelli Fabio Tolomelli Alessandra |
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| Institution: | Department of Chemistry G. Ciamician, University of Bologna, Via Selmi 2, 40126 Bologna, Italy. giuliana.cardillo@unibo.it |
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| 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 toward the (E)- or (Z)-isomer, useful precursors of 3(2'-amino)-beta-lactams. reaction: see text] |
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