Stannane-free chemoselective hydrodehalogenation of 4-halotetrahydropyrans: scope and application to natural product synthesis.

A stannane-free hydrodehalogenation of 4-halotetrahydropyran under very mild conditions has been developed. This methodology allows selective one-pot dehalogenation and/or debenzylation depending on the type of halide-substrate used. The applicability of this methodology is well demonstrated in the synthesis of a key intermediate toward the enantioselective synthesis of (+)-SCH 351448.