Diastereoselective Conjugate Addition of Organoboron Nucleophiles

Significance

The stereoselectivity of the addition of boronic acids to conjugated systems bearing an oxygen at the γ-position was shown to be completely selective for the anti product (3, 5 and 7). The conformation of the alkene did not influence the stereochemical outcome, as both E- and Z-enoates gave the anti product. Furthermore, protection of the hydroxyl group was shown to be unnecessary.