高非对映选择性烯丙基叠氮化物的形成与异构化。3(2'-氨基)-β-内酰胺的合成。
Highly diastereoselective allylic azide formation and isomerization. Synthesis of 3(2'-amino)-beta-lactams.
作者信息
Cardillo Giuliana, Fabbroni Serena, Gentilucci Luca, Perciaccante Rossana, Piccinelli Fabio, Tolomelli Alessandra
机构信息
Department of Chemistry G. Ciamician, University of Bologna, Via Selmi 2, 40126 Bologna, Italy.
出版信息
Org Lett. 2005 Feb 17;7(4):533-6. doi: 10.1021/ol047815n.
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]
叠氮化钠对3-烯基-3-溴氮杂环丁烷-2-酮进行立体选择性反SN2'进攻，得到非对映异构叠氮化物的混合物，处于快速平衡状态。烯丙基叠氮化物的[3,3]-σ迁移重排具有完全的立体控制，使平衡优先导向（E）-或（Z）-异构体，它们是3(2'-氨基)-β-内酰胺的有用前体。[反应：见正文]
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