Molybdenum-mediated diastereoselective synthesis of 2-heterobicyclo[4.4.0]decene derivatives

Abstract

The addition of a variety of functionalized zinc–copper reagents RCu(CN)ZnI 2 to (η⁵-cyclopentadienyl)(η⁴-cyclohexa-1,3-diene)dicarbonylmolybdenum cation 1 proceeds in a highly regio- and stereo-specific fashion to generate (η⁵-cyclopentadienyl)(π-allyl)dicarbonylmolybdenum complexes 3 with a functionalized side-chain at the C-4 position of the ring. Intramolecular cyclization of the (π-allyl)molybdenum complexes containing a pendant alcohol, carboxylic acid, thiol or amine functionality affords fused 2-heterobicyclo[4.4.0]decene derivatives.