Functional Group Interconversion of Alkylidenemalononitriles to Primary Alcohols by a Cooperative Redox Operation
Functional Group Interconversion of Alkylidenemalononitriles to Primary Alcohols by a Cooperative Redox Operation
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DOI：
10.1055/s-0040-1707184
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发表时间：
2020-07
期刊：
影响因子：
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通讯作者：
Alexander J. Grenning;Fabien Emmetiere
中科院分区：
文献类型：
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作者：
Alexander J. Grenning;Fabien Emmetiere
摘要官能团间的相互转化是实现合成的重要化学过程。在这份报告中，我们描述了一种策略，将亚烷基丙二腈转化为伯醇在一个步骤。该反应依赖于一个精心设计的氧化还原过程，包括亚烷基还原，丙二腈氧化和酰基氰还原，其中分子氧和NaBH 4协同工作。该方法适用于各种碳骨架，并用于合成复杂的萜类化合物架构。
Abstract Functional group interconversions are essential chemical processes enabling synthesis. In this report, we describe a strategy to convert alkylidenemalononitriles into primary alcohols in one step. The reaction relies on a choreographed redox process involving alkylidene reduction, malononitrile oxidation, and acylcyanide reduction where molecular oxygen and NaBH4 work cooperatively. The method was applied to a variety of carbon skeletons and was utilized to synthesize complex terpenoid architectures.