Integrated Experimental and Computational Studies on the Organocatalytic Kinetic Resolution of β-Unfunctionalized Primary Alcohols Using a Chiral 1,2-Diamine: The Importance of Noncovalent Interactions
Integrated Experimental and Computational Studies on the Organocatalytic Kinetic Resolution of β-Unfunctionalized Primary Alcohols Using a Chiral 1,2-Diamine: The Importance of Noncovalent Interactions
复制标题
DOI：
10.1021/acs.joc.1c03033
复制
发表时间：
2022-03-18
影响因子：
3.6
通讯作者：
Oriyama，Takeshi
中科院分区：
文献类型：
--
作者：
Sakai，Naoki;Ojima，Kohei;Oriyama，Takeshi
在催化量的一种新的手性（S）-脯氨酸衍生的1，2-二胺存在下，用苯甲酰氯对β-非官能化伯醇进行了不对称动力学拆分。合成了几种有价值的手性2-取代丙醇，具有良好的对映选择性。密度泛函理论计算表明，非共价相互作用，如CH−π相互作用，是对映选择性的决议至关重要。这项研究是通过实验和计算之间的相互作用。
The enantioselective kinetic resolution of β-unfunctionalized primary alcohols with benzoyl chloride was carried out in the presence of a catalytic amount of a novel chiral 1,2-diamine derived from (S)-proline. Several valuable chiral 2-substituted propan-1-ols were obtained with good enantioselectivities. Density functional theory calculations revealed that the noncovalent interaction, such as CH−π interaction, is crucial for the enantioselectivity of the resolution. This study was conducted through an interplay between experiment and computation.