Enantioselective Synthesis of <i>trans</i>-Aryl- and -Heteroaryl-Substituted Cyclopropylboronates by Copper(I)-Catalyzed Reactions of Allylic Phosphates with a Diboron Derivative
2010-08-25T00:00:00Z (GMT) by
A new asymmetric route for the synthesis of <i>trans</i>-2-aryl- and -heteroaryl-substituted cyclopropylboronates has been developed. (<i>Z</i>)-3-arylallylic phosphates were converted to the optically active products with high yield and diastereo- and enantioselectivity through a copper(I)-catalyzed reaction with a diboron derivative. Under mild reaction conditions, the reaction affords the arylcyclopropane products with a functional group and a heteroaromatic group in a highly enantioselective manner. When (<i>E</i>)-allylic phosphates were used as substrates, a ligand-controlled product switch between the trans and cis configurations was observed.