Copper-Catalyzed Enantioselective Domino Arylation/Semipinacol Rearrangement of Allylic Alcohols with Diaryliodonium Salts.
A copper-catalyzed enantioselective arylative semipinacol rearrangement of allylic alcohols was developed. In the presence of a catalytic amount of an in situ generated chiral copper-bisoxazoline complex, reaction of allylic alcohols with diaryliodonium salts afforded spirocycloalkanones in high yields with high diastereo- and enantioselectivities. A two-point binding model engaging the carbon-carbon double bond and the proximal hydroxyl group was proposed to be responsible for the highly efficient chirality transfer.
['Wu|Hua|H|', 'Wang|Qian|Q|', 'Zhu|Jieping|J|http://orcid.org/0000-0002-8390-6689']
semipinacol rearrangement diaryliodonium salt asymmetric catalysis homogeneous catalyst ring expansion