D. Stien, D. Crich, M. Bertrand
Sep 3, 1998
Citations
0
Influential Citations
16
Citations
Journal
Tetrahedron
Abstract
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.