Synthesis of Amino-Substituted Indanes and Tetralins via Consecutive Multibond-Forming Tandem Processes

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• 作者：Mark W. Grafton ; Louis J. Farrugia ; Andrew Sutherland
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：July 19, 2013
• 年：2013
• 卷：78
• 期：14
• 页码：7199-7207
• 全文大小：378K
• 年卷期：v.78,no.14(July 19, 2013)
• ISSN：1520-6904

文摘

A rapid and general approach for the synthesis of amino-substituted indanes and tetralins from readily available alkyne-derived allylic alcohols via consecutive multibond-forming tandem processes has been developed. In the first one-pot tandem process, a series of cyclic dienes were prepared using an Overman rearrangement under thermal conditions, followed by a ruthenium(II)-catalyzed ring closing enyne metathesis reaction. The resulting exo-dienes were then subjected to a second one-pot tandem process involving a highly regioselective Diels鈥揂lder reaction with alkynes, quinones or nitriles and a subsequent oxidation step to give a diverse library of C-1 amino-substituted indanes and tetralins in good overall yields.