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2004
Multicomponent reactions
O 0359
A Highly Diastereoselective Tandem Radical Reaction. Facile Three-Component
to Protected (E)-Polysubstituted Homoallylic Alcohols. — In this tandem
47- 054 Routes
radical coupling of olefins and (E)-β-nitrostyrenes with benzoyl peroxide, stereodefined homoallylic benzoyl-protected alcohols are prepared in good to moderate yields.
Various Lewis acids are evaluated in the diastereoselective radical substitution with
nitrostyrenes (I). Titanium (IV) 2-ethylhexoxide is found to be the best Lewis acid in
terms of yield and diastereoselectivity (up to 98% d.e.). The utility and generality of
the method is demonstrated by tandem radical cyclizations with cyclooctadiene affording the fused ring system (VIII). — (JANG, Y.-J.; WU, J.; LIN, Y.-F.; YAO*, C.-F.;
Tetrahedron 60 (2004) 31, 6565-6574; Dep. Chem., Natl. Taiwan Norm. Univ.,
Taipei 116, Taiwan; Eng.) — Bartels
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