Moon Patrick J, Wei Zhongyu, Lundgren Rylan J
Department of Chemistry , University of Alberta , Edmonton , Alberta T6G 2G2 , Canada.
J Am Chem Soc. 2018 Dec 19;140(50):17418-17422. doi: 10.1021/jacs.8b11390. Epub 2018 Dec 4.
We demonstrate that metal-catalyzed enantioselective benzylation reactions of allylic electrophiles can occur directly from aryl acetic acids. The reaction proceeds via a pathway in which decarboxylation is the terminal event, occurring after stereoselective carbon-carbon bond formation. This mechanistic feature enables enantioselective benzylation without the generation of a highly basic nucleophile. Thus, the process has broad functional group compatibility that would not be possible employing established protocols.
我们证明,烯丙基亲电试剂的金属催化对映选择性苄基化反应可以直接从芳基乙酸发生。该反应通过一条途径进行,其中脱羧是末端事件,发生在立体选择性碳-碳键形成之后。这种机理特征使得对映选择性苄基化反应无需生成高碱性亲核试剂。因此,该过程具有广泛的官能团兼容性,这是采用既定方案所无法实现的。