Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States.
J Org Chem. 2023 Jun 2;88(11):7560-7563. doi: 10.1021/acs.joc.3c00535. Epub 2023 May 9.
Remote stereocontrol in the Ireland-Claisen rearrangement using a chiral acetonide that serves as internal stereocontrol element is an effective and general method for chirality transfer from a δ-hydroxyl group in the allylic alcohol unit. This strategy circumvents the need for redundant chirality at the α-position allylic alcohol, while simultaneously producing a terminal alkene that can streamline synthetic applications and complex molecule synthesis planning.
使用手性缩酮作为内部立体控制元件的爱尔兰-Claisen 重排的远程立体控制是一种从烯丙醇单元的 δ-羟基有效且通用的手性转移方法。该策略避免了α-位烯丙醇中冗余手性的需要，同时生成了末端烯烃，这可以简化合成应用和复杂分子合成计划。
