Rhodium-Catalyzed Asymmetric 1,4-Addition of Organoboron Reagents to 5,6-Dihydro-2(1<i>H</i>)-pyridinones. Asymmetric Synthesis of 4-Aryl-2-piperidinones
作者:Taichi Senda、Masamichi Ogasawara、Tamio Hayashi
DOI:10.1021/jo0103930
日期:2001.10.1
Catalytic asymmetric synthesis of 4-aryl-2-piperidinones was realized for the first time by asymmetric 1,4-addition of arylboron reagents to 5,6-dihydro-2(1H)-pyridinones in the presence of a chiral bisphosphine-rhodium catalyst. In the reaction introducing 4-fluorophenyl group, the use of 4-fluorophenylboroxine and 1 equiv (to boron) of water at 40 degrees C gave the highest yield of the arylation
在手性双膦-铑催化剂存在下,芳基硼试剂向5,6-二氢-2(1H)-吡啶酮的不对称1,4-加成反应,首次实现了4-芳基-2-哌啶酮的催化不对称合成。 。在引入4-氟苯基的反应中,在40℃下使用4-氟苯基环硼氧烷和1当量(对硼)的水以最高的对映选择性(98%ee)得到最高的芳基化产物产率。此处获得的(R)-4-(4-氟苯基)-2-哌啶酮是合成(-)-帕罗西汀的关键中间体。