Iron-catalyzed regio- and stereoselective ring opening of [2.2.1]- and [3.2.1]oxabicyclic alkenes with a Grignard reagent.

Abstract

[reaction: see text] Arylative and alkenylative ring-opening reactions of a [2.2.1]- or [3.2.1]oxabicyclic alkene with a Grignard reagent take place in the presence of a catalytic amount of iron(III) chloride and a stoichiometric amount of TMEDA to produce a highly substituted 3-cyclohexen-1-ol or 3-cyclohepten-1-ol in good yield with high regio- and stereoselectivity.