使用催化量的二碘化钐或三碘化钐从α,β-环氧酰胺高选择性合成(E)-α-羟基-β,γ-不饱和酰胺。
Synthesis of (E)-alpha-hydroxy-beta,gamma-unsaturated amides with high selectivity from alpha,beta-epoxyamides by using catalytic samarium diiodide or triiodide.
作者信息
Concellón José M, Bernad Pablo L, Bardales Eva
机构信息
Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, E-33071 Oviedo, Spain.
出版信息
Chemistry. 2004 May 17;10(10):2445-50. doi: 10.1002/chem.200305375.
The highly stereoselective synthesis of (E)-alpha-hydroxy-beta,gamma-unsaturated amides starting from alpha,beta-epoxyamides, by using catalytic SmI2 or SmI3, was achieved. This transformation can also be carried out by using SmI2 generated in situ from samarium powder and diiodomethane. The starting compounds 1 are easily prepared by the reaction of enolates derived from alpha-chloroamides with ketones at -78 degrees C. A mechanism to explain this transformation has been proposed. Cyclopropanation of (E)-alpha-hydroxy-beta,gamma-unsaturated amides has been performed to demonstrate their synthetic applications.
实现了从α,β-环氧酰胺出发，使用催化量的SmI2或SmI3对(E)-α-羟基-β,γ-不饱和酰胺进行的高立体选择性合成。该转化也可以通过用钐粉和二碘甲烷原位生成的SmI2来进行。起始化合物1很容易通过α-氯代酰胺衍生的烯醇盐在-78℃下与酮反应制备。已经提出了一种解释这种转化的机理。对(E)-α-羟基-β,γ-不饱和酰胺进行了环丙烷化反应以证明其合成应用。
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