Li Hao, Loh Teck-Peng
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore.
J Am Chem Soc. 2008 Jun 11;130(23):7194-5. doi: 10.1021/ja801488z. Epub 2008 May 20.
Mukaiyama-Aldol and Prins reactions have been identified as highly efficient methods in C-C bond formation since they were discovered several decades ago. Since both reactions gave the same common intermediate, oxocarbonium, we intend to combine the two reactions into a domino process, which means the formation of multiple C-C bonds and stereogenic centers in one pot without isolation of any intermediates. We envisage that the domino reactions involving the Mukaiyama-Aldol reaction of silyl enol ether and acetal treated with Lewis acid (TiBr4) will produce an oxonium intermediate which upon trapping by an alkene functionality in an intramolecular Prins cyclization will generate the cyclopentyl ring system.
自从几十年前被发现以来，向山-羟醛反应和普林斯反应已被视为碳-碳键形成的高效方法。由于这两种反应都生成相同的常见中间体——氧鎓离子，我们打算将这两种反应合并为多米诺反应过程，即在不分离任何中间体的情况下，一锅法形成多个碳-碳键和立体中心。我们设想，涉及用路易斯酸（TiBr4）处理的硅烯醇醚和缩醛的向山-羟醛反应的多米诺反应将生成一个氧鎓中间体，该中间体在分子内普林斯环化反应中被烯烃官能团捕获后将生成环戊基环系。
