Chiral lactones are found in many natural products. The reaction of simple alkenes with iodoacetic acid is a powerful method to build lactones, but the enantioselective version of this reaction has not been implemented to date. Herein, we report the efficient catalytic radical enantioselective carbo-esterification of styrenes enabled by a newly developed Cu I -perfluoroalkylated PyBox system. Simple styrenes have been converted to useful chiral lactones, whose synthetic applications are showcased. Mechanistic studies reveal that this reaction is a rare example of an efficient liganddecelerated system, in which the ligand decelerates the reaction, but the reaction is still efficient with reduced amounts of ligand. This uncommon catalytic system may inspire further consideration of the effect of ligands in asymmetric catalysis.
Compared to universal radical difunctionalization of alkenes that are performed with organic solvents, such reactions with water as the sole solvent are rarely reported. Concerning the global consensus on environmental issues, we developed herein a method for radical oxyazidation of alkenes in pure water. This reaction allows the constructions of C-N and C-O bonds in a one pot process. Styrenes, 1,3-dienes, and unactivated alkenes can react smoothly under mild and environmentally benign conditions to afford a wide scope of functionalized azides in excellent yields and selectivity.
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