通过N-乙烯基-β-内酰胺的扩环反应合成氨基环丁烷。
Synthesis of aminocyclobutanes through ring expansion of N-vinyl-beta-lactams.
作者信息
Cheung Lawrence L W, Yudin Andrei K
机构信息
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto M5S 3H6, Canada.
出版信息
Org Lett. 2009 Mar 19;11(6):1281-4. doi: 10.1021/ol900118d.
PMID:19239262
Abstract
Both eight-membered enamide rings and fused [4.2.0]aminocyclobutane-containing delta-lactams can be accessed from N-vinyl-beta-lactams. The eight-membered rings are made through a [3,3] sigmatropic rearrangement. At elevated temperature, the eight-membered lactam undergoes electrocyclization to furnish fused cyclobutane delta-lactams in a diastereoselective manner.
摘要
八元烯酰胺环和含稠合[4.2.0]氨基环丁烷的δ-内酰胺均可由N-乙烯基-β-内酰胺制得。八元环是通过[3,3]σ迁移重排形成的。在升高的温度下，八元内酰胺发生电环化反应，以非对映选择性的方式生成稠合环丁烷δ-内酰胺。
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