Photocatalytic delayed hydration by alkene-alkene coupling: Modular access to highly substituted γ- and δ-lactones
Yu-Feng Ren1, Jin-Kui Chen1, Xiao-Yi Chen1
1Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Shenzhen Grubbs Institute, Department of Chemistry, and Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, Guangdong, P. R. China.
None:
γ- and δ-lactones are important core structures in a wide range of natural products and bioactive molecules. However, a gap remains for rapid access to γ- and δ-lactones from easily available and simple starting materials with tunability for substitution patterns. Here, a photocatalytic "streamlined sew" strategy of two alkenes with water for the synthesis of γ- and δ-lactones by a [1 + 2 + 2] or [1 + 2 + 3] cyclization has been developed. The reaction features the delayed hydration of alkenes by differentiating different alkyl radicals to undergo chemo- and regioselective alkene-alkene cross-coupling. Notably, styrenes, tetra-, tri-, and disubstituted aliphatic alkenes are tolerated in the reaction, allowing for rapid and modular assembly of γ- and δ-lactones from two alkenes in the presence of water.
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