Efficient Pyrrole Synthesis Using Double Nucleophilic Addition to α,β-Unsaturated Imines with Plural Nucleophiles
Efficient Pyrrole Synthesis Using Double Nucleophilic Addition to α,β-Unsaturated Imines with Plural Nucleophiles
复制标题
DOI：
10.1021/ol0615634
复制
发表时间：
2006-07
期刊：
影响因子：
5.2
通讯作者：
M. Shimizu;A. Takahashi;S. Kawai
中科院分区：
文献类型：
--
作者：
M. Shimizu;A. Takahashi;S. Kawai
通过将 α,α-二烷氧基烯酮甲硅烷基缩醛和烯酮甲硅烷基硫缩醛或三甲基甲硅烷基氰化物双亲核加成到 α,β-不饱和亚胺上，然后进行酸促进环化和 DDQ 氧化，以区域选择性方式制备 2,3,5-三取代吡咯。使用该方法合成了具有单吡咯醛部分的咪唑甘油磷酸脱水酶抑制剂（IGPDI）。
2,3,5-Trisubstituted pyrroles were prepared in a regioselective manner using the double nucleophilic addition of α,α-dialkoxy ketene silyl acetals and ketene sily thioacetals or trimethylsilyl cyanide to α,β-unsaturated imines followed by acid-promoted cyclization and oxidation with DDQ. Using this methodology an imidazole glycerol phosphate dehydratase inhibitor (IGPDI) possessing a monopyrrole aldehyde moiety was synthesized.