Cu-Catalyzed SN2′ Substitution of Propargylic Phosphates with Vinylarene-Derived Chiral Nucleophiles: Synthesis of Chiral Allenes

A new Cu-catalyzed enantioselective three component (i.e., styrenes, B(2)pin(2), and propargylic phosphates) allenylation via an S(N)2' substitution of propargylic electrophiles with vinylarene-derived chiral nucleophiles is presented. This method provides an efficient and enantioselective approach to access a range of optically pure di-(1,1-), tri-, and tetra-substituted allenes with alpha-central chirality and axial chirality in excellent chemo-, regio-, diastereo-, and enantioselectivities.