Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University , SE-10691 Stockholm, Sweden.
Org Lett. 2017 Apr 7;19(7):1622-1625. doi: 10.1021/acs.orglett.7b00433. Epub 2017 Mar 23.
In this study, we present the synthesis of new, stereodefined allylboronic acids employed to investigate the stereochemistry of the Cu-catalyzed cross-coupling of allylboronic acids with α-diazoketones. According to our results, this reaction proceeds with retention of the relative configuration of the allylboronic acid substrate. We suggest that the stereoinduction step involves a syn S2'-type transmetalation of the allylboronic acid substrate with a Cu-carbene species.
在这项研究中，我们提出了新的、立体确定的烯丙基硼酸的合成方法，用于研究 Cu 催化的烯丙基硼酸与α-重氮酮的交叉偶联反应的立体化学。根据我们的结果，该反应以烯丙基硼酸底物的相对构型保留的方式进行。我们提出，立体诱导步骤涉及烯丙基硼酸底物与 Cu-卡宾物种的顺 S2'型转金属化。
