Abstract
Chiral 1,3-dioxolan-2-yl radicals derived from acetals 8 and 9 underwent intramolecular hydrogen abstraction followed by 5-exo-trig cyclization on treatment with tributyltin hydride and AIBN with modest and opposite stereoselectivities. The more highly substituted substrate 13 took part in a similar cascade, triggered by a 5- exo-dig cyclization. In this example the more highly substituted nature of the alkene in the stereocontrolled cyclization resulted in essentially complete diastereoselectivity.
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