Palladium-catalyzed asymmetric allylic alkylation with an enamine as the nucleophilic reagent

Palladium-catalyzed asymmetric allylic alkylation with an enamine as the nucleophilic reagent
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以烯胺为亲核试剂的钯催化不对称烯丙基烷基化

DOI:
10.1016/j.tetlet.2007.08.119
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发表时间:
2007-10-22
影响因子:
1.8
通讯作者:
Zhang, Wanbin
Zhang, Wanbin
中科院分区:
化学4区
文献类型:
--
作者:
Liu, Delong;Xie, Fang;Zhang, Wanbin

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烯胺可以作为钯催化的不对称烯丙基烷基化反应的良好亲核试剂,避免了使用强碱形成的不稳定的酮烯醇化物。该反应在手性双烯膦恶唑啉钯配合物存在下进行,具有较高的催化活性和良好的对映选择性。二茂铁和二茂茂碳环之间的距离不同影响了它们在反应中的催化行为。此外,仅具有平面手性的二茂铁双膦配体也具有高的催化活性和良好的对映选择性。(C)2007爱思唯尔有限公司版权所有。
An enamine can serve as a good nucleophile for palladium-catalyzed asymmetric allylic alkylation, avoiding the use of an unstablilized ketone enolate formed by strong bases. In the presence of a palladium complex of chiral metallocene-based phosphino-oxazoline ligands, the reaction was carried out smoothly with high catalytic activity and excellent enantioselectivity. Different distances between the two Cp rings of ferrocene and ruthenocene affected the catalytic behavior in the reaction. Furthermore, high catalytic activity and good enantio selectivity were also afforded by the ferrocene-based diphosphine ligands with only planar chirality. (C) 2007 Elsevier Ltd. All rights reserved.