Highly selective SmI2–H2O-promoted radical cyclisation of five-membered lactones

Radicals formed by SmI2–H2O-mediated electron transfer to the carbonyl group of unsaturated five-membered lactones undergo diastereoselective cyclisation to give cyclohexane-1,4-diols. The use of HMPA as an additive with SmI2–H2O gave improved conversion and diastereoselectivity in the cyclisations.

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