Silyl-Group-Directed Linear-Selective Allylation of Carbonyl Compounds with Trisubstituted Allylboronates Using a Copper(I) Catalyst,ACS Catalysis

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Silyl-Group-Directed Linear-Selective Allylation of Carbonyl Compounds with Trisubstituted Allylboronates Using a Copper(I) Catalyst
ACS Catalysis ( IF 11.3 ) Pub Date : 2020-02-03 , DOI: 10.1021/acscatal.9b05408
Hiroaki Iwamoto ₁ , Yuta Hayashi ₁ , Yu Ozawa ₁ , Hajime Ito _{1,

2}

Affiliation

A copper(I)-catalyzed linear-selective allylation of carbonyl compounds with trisubstituted allylboronates has been achieved by capitalizing on the electronic and steric effects of silyl groups. This reaction provides stereodefined trisubstituted homoallyl alcohol derivatives that bear a synthetically useful alkenyl silane moiety. The results of a computational study suggested that the silyl directing group thermodynamically stabilizes the sterically hindered allylcopper(I) intermediate and kinetically facilitates the carbonyl allylation path for the linear product by lowering the energy of its transition state.

中文翻译：

使用铜（I）催化剂的羰基化合物与三取代的烯丙基硼酸酯的甲硅烷基定向的线性选择性烯丙基化

通过利用甲硅烷基的电子和空间效应，已经实现了羰基化合物与三取代的烯丙基硼酸酯的铜（I）催化的线性选择性烯丙基化。该反应提供了带有合成上有用的烯基硅烷部分的立体确定的三取代的均烯丙基醇衍生物。计算研究的结果表明，甲硅烷基导向基团可热力学稳定位阻的烯丙基铜（I）中间体，并通过降低其过渡态能量而动力学上促进线性产物的羰基烯丙基化途径。

更新日期：2020-02-04

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