Resolution of Allylic Alcohols via Copper(I) Complexes with a Chiral Diamine

By using the Corey diamine 1,2-diphenyl-N,N′-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane, Copper(I) olefin complexes are prepared. When the olefin is a racemic allylic alcohol, selective coordination of one enantiomer is observed. Cleavage with aqueous HCl or NaCN allows a two-steps resolution affording excellent enantiomeric excess.