通过烯醇锌盐与未活化炔烃加成实现四取代烯烃的立体选择性合成。
Stereoselective synthesis of tetra-substituted olefins via addition of zinc enolates to unactivated alkynes.
作者信息
Nakamura Masaharu, Fujimoto Taisuke, Endo Kohei, Nakamura Eiichi
机构信息
Department of Chemistry, University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
出版信息
Org Lett. 2004 Dec 23;6(26):4837-40. doi: 10.1021/ol048131i.
[reaction: see text] In the presence of a stoichiometric or catalytic amount of diethylzinc, a beta-aminocrotonamide undergoes sequential addition/isomerization reactions with 1-alkyne to produce, upon hydrolysis, an alpha-alkylidene beta-dicarbonyl compound in a highly stereoselective manner. The method complements the conventional Knoevenagel synthesis of this class of compounds as to the choice of the starting material and the scope and stereochemistry of the product.
[反应：见正文] 在化学计量或催化量的二乙基锌存在下，β-氨基巴豆酰胺与1-炔烃发生连续加成/异构化反应，水解后以高度立体选择性的方式生成α-亚烷基β-二羰基化合物。该方法在起始原料的选择以及产物的范围和立体化学方面补充了此类化合物的传统克诺文纳格尔合成法。
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