通过铝催化肟亲核试剂的共轭加成实现α,β-不饱和酰亚胺的对映选择性形式水合反应。
Enantioselective formal hydration of alpha,beta-unsaturated imides by Al-catalyzed conjugate addition of oxime nucleophiles.
作者信息
Vanderwal Christopher D, Jacobsen Eric N
机构信息
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA.
出版信息
J Am Chem Soc. 2004 Nov 17;126(45):14724-5. doi: 10.1021/ja045563f.
The (salen)Al-catalyzed asymmetric conjugate addition of salicylaldoxime to alpha,beta-unsaturated imides is the key step in an efficient and highly enantioselective two-step formal hydration of these electron-deficient olefins. This reaction constitutes the first example of an enantioselective conjugate addition of an oxygen-centered nucleophile to alpha,beta-unsaturated carboxylic acid derivatives. Application of this method to chiral, nonracemic substrates revealed a high level of catalyst-induced diastereoselectivity, underscoring its potential utility for polyketide natural product synthesis.
（水杨醛缩邻氨基苯酚）铝催化的水杨醛肟与α,β-不饱和酰亚胺的不对称共轭加成反应，是这些缺电子烯烃高效且高对映选择性两步形式水合反应中的关键步骤。该反应是氧中心亲核试剂对α,β-不饱和羧酸衍生物进行对映选择性共轭加成的首个实例。将此方法应用于手性、非外消旋底物时，显示出高水平的催化剂诱导非对映选择性，突出了其在聚酮天然产物合成中的潜在应用价值。
Zotero 插件