Radical Cyclization of Bromomethyldimethylsilyl Propargyl Ethers. Diastereoselective Synthesis of Functionalized Cyclopentanone Precursorsviaa (1,5) Hydrogen-Atom Transfer.

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Abstract
A (1,5) hydrogen shift, involved in the radical cyclization of acetal ω-yne compounds, led to cyclopentanone precursors in high yields. This one-pot reaction allowed the stereocontrolled formation of two contiguous stereogenic centers from two sp hybridized carbons. When a homoallylic double bond was present in the starting material, the reaction was totally chemoselective in favor of a 5-exo-trig process.

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