A highly enantioselective, moderately anti-selective aldol reaction using a novel hydrazone moiety as stereo director
作者:Gerard P. McGlacken、Simon W. Breeden
DOI:10.1016/j.tetasy.2005.09.027
日期:2005.11
with a view to develop a highly enantioselective, anti-diastereoselective aldol addition procedure has been investigated. A number of proline-derived hydrazones were produced and their effectiveness in directing simple alkylation of aza-enolates investigated. The most promising of these hydrazones were then used in the aldol reaction. The substituent on the oxygen of the proline had a profound effect
为了开发高度对映选择性,反非对映选择性的醛醇加成方法,已经研究了使用新型作为立体导向剂。产生了许多脯氨酸衍生的azo,并研究了它们在指导简单的氮杂-烯醇酸酯烷基化反应中的有效性。然后将这些promising中最有希望的用于醛醇缩合反应。脯氨酸的氧上的取代基对幅度和不对称感应感都具有深远的影响。戊酮与丙醛之间进行正式羟醛反应的最佳给出了37%的非对映选择性,有利于抗异构体,而两种异构体的ee均为83-84%。