Molecular-Oxygen-Mediated Multicomponent Oxidative Cyclization: Synthesis of Tertiary-Alcohol-Unit-Bearing
Xiaoshuang Guo1,2, Maozhong Miao2, Peng Zhao1
1Institute of Advanced Studies and School of Pharmaceutical Sciences, Taizhou University, Jiaojiang, Zhejiang 318000, China.
Abstract:
We developed a molecular-oxygen-mediated multicomponent oxidative cyclization strategy to synthesize N-heterocycles containing tertiary alcohol units via the formation of key C-OH bonds and quaternary carbon centers. This formal [3 + 2 + 1] annulation offers a green and sustainable alternative for the de novo C-OH bond formation, using O2 as both the oxidant and oxygen source under metal- and catalyst-free conditions. Notably, continuous [1,5]-hydrogen transfer together with excess alcohols promotes the formation of C-OH-bearing products. Additionally, the generation of quaternary carbon centers inhibits the conversion of C-OH bonds to C═O bonds, thus stabilizing the desired products.
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