超硅基作为羧酸保护基：在高度立体选择性的羟醛缩合和曼尼希反应中的应用。
The supersilyl group as a carboxylic acid protecting group: application to highly stereoselective aldol and Mannich reactions.
机构信息
Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637, USA.
出版信息
Angew Chem Int Ed Engl. 2013 Jul 8;52(28):7198-202. doi: 10.1002/anie.201300102. Epub 2013 May 29.
Abstract
: The application of the "supersilyl” group as carboxylic acid protecting group has been investigated. The unique properties of the “supersilyl” group enabled it to outperform typical carboxyl protecting groups, conferring extraordinary protection upon the carboxyl functionality. “Supersilyl” esters were also utilized for the first time as stable carboxylic acid synthetic equivalents in highly stereoselective aldol and Mannich reactions. The value of this methodology has been further described by the easy photo-deprotection protocol and its applications in rapid synthesis of polyketide subunits.
摘要
: 我们研究了“超硅基”基团在羧酸保护基中的应用。“超硅基”基团的独特性质使其优于典型的羧基保护基，为羧基官能团提供了非凡的保护。“超硅基”酯也首次被用作高度立体选择性羟醛缩合和曼尼希反应中稳定的羧酸合成等价物。这种方法的价值还通过易于光解的脱保护方案及其在聚酮亚基快速合成中的应用得到了进一步描述。
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