Skeletal Rearrangement of Oxazole to Azepine and Pyrrole through Dynamic 8π Electrocyclizations

作者：Yi Tian, Lei Liu, Tu Zeng, Qian Wu, Baosheng Li · 发表于：Organic Letters · 年份：2024 · DOI：10.1021/acs.orglett.4c00826 · 被引用次数：13 · 研究领域：Cyclopropane Reaction Mechanisms、Catalytic C–H Functionalization Methods、Catalytic Cross-Coupling Reactions

We present a novel approach for the skeletal rearrangement of an oxazole into an azepine and pyrrole through a dynamic electrocyclization process, showing an innovative, unconventional reaction sequence. This method enables precise control of regioselectivity in competitive 6π and 8π electrocyclization reactions, rendering the final products rich in functional groups that can be further developed for the synthesis of nitrogen-containing scaffolds. This is an unprecedented example of the selective synthesis of seven- and five-member heterocycles via dynamic electrocyclization ring opening or closure.