On-DNA Three-Component Cycloaddition of Diazo Compounds, Nitrosoarenes, and Alkenes: Syntheses of Isoxazolidines for DNA-Encoded Chemical Libraries
Xiang Fu, Yaxin Li, Mingjin He, Junxin Ren, Zinan Wei, Zhenghui Kang, Wenhao Hu
Abstract
A DNA-compatible three-component reaction is disclosed for the synthesis of on-DNA polysubstituted isoxazolidines that serve as privileged core scaffolds in numerous natural products and bioactive molecules. This one-pot approach involves the 1,3-dipolar cycloaddition of DNA-tagged styrenes with diazo compounds and nitrosoarenes in an aqueous solution of KOAc. The reaction demonstrates excellent functional group compatibility, providing a conventional protocol for the construction of a DNA-labeled isoxazolidine library.
Topics & Concepts
ChemistryCycloadditionDiazoDNACombinatorial chemistryMoleculeFunctional groupOrganic chemistryCatalysisBiochemistryPolymerCyclopropane Reaction MechanismsSynthesis and Catalytic ReactionsChemical Synthesis and Analysis