Smith Amos B, Xian Ming
Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, PA 19104, USA.
J Am Chem Soc. 2006 Jan 11;128(1):66-7. doi: 10.1021/ja057059w.
An effective one-flask multicomponent linchpin coupling protocol employing the concept of anion relay chemistry (ARC) was developed. This concept calls for addition of an anion (5) to an epoxide (6), bearing on a distal carbon a trialkyl silyl group and an anion stabilizing group (ASG), to furnish upon epoxide ring opening oxyanion 7. Addition of HMPA or other polar solvents to trigger a solvent controlled 1,4-Brook rearrangement then leads to a new distal anion (8), which in turn is available to react with a variety of second electrophiles.
开发了一种有效的单瓶多组分关键偶联方案，该方案采用了阴离子中继化学（ARC）的概念。这一概念要求将阴离子（5）添加到环氧化物（6）上，该环氧化物在远端碳上带有三烷基硅基和阴离子稳定基团（ASG），以使环氧化物开环时生成氧阴离子7。添加HMPA或其他极性溶剂以引发溶剂控制的1,4-布鲁克重排，进而生成新的远端阴离子（8），该阴离子又可与多种第二亲电试剂反应。
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