Regioselective Cuprate Additions to Tethered Allylic Phosphates

Significance

The method allows the preparation of enantiopure alkyl-substituted homoallylic alcohols. The phosphate group is used both as a tether to ensure the Z-conformation of the alkene from two allylic alcohols, and as diastereotopic leaving group. In the case of non-symmetrical bis-allylic phosphates 4 and 6, the most substituted phosphate C-O bond is the leaving group. The allylic phosphates can be prepared in three steps and offer the advantage that different bis-allylic alcohols can be easily prepared.