Asymmetric Iodonio-[3,3]-Sigmatropic Rearrangement to Access Chiral α-Aryl Carbonyl Compounds
Junsong Tian, Fan Luo, Qifeng Zhang, Yuchen Liang, Dongyang Li, Yaling Zhan, Lichun Kong, Zhixiang Wang, Bo Peng
Abstract
Here we describe an asymmetric [3,3]-sigmatropic rearrangement of aryl iodanes that enables the enantioselective α-arylation of chiral 2-oxazolines, thereby producing valuable chiral α-aryl carbonyl compounds. The success of this protocol hinges on the selective assembly of aryl iodanes with 2-oxazolines and the smooth deprotonation of the in situ-generated iodonium-imine species. The nearly neutral and mild conditions of the reaction allow it to tolerate a wide variety of functional groups. Moreover, the remaining iodine atom in the products not only provides a versatile platform for further elaboration of such molecules but also supplies the asymmetric hypervalent iodine chemistry with a new class of chiral scaffolds.