Enantioselective Alkylative Ring Opening of Heterobicyclic Alkenes via Fesulphos Ligands

Significance

The enantioselective ring opening of meso heterobicyclic alkenes is a useful reaction which can give fast access to chiral, heteroatom-containing products. Although the enantioselective alkylative ring opening of heterobicyclic alkenes is known, development of new ligands can allow problematic cases to be improved. The family of Fesulphos ligands were found to be highly effective in the addition of dialkylzinc reagents to a variety of oxa- and azabicyclic alkenes. Yields are generally good, and enantiomeric excesses generally approach or exceed known cases.