Asymmetric Wittig reactions of chiral arsonium ylides. Part 2: Atroposelective olefination of axially chiral N,N-dialkyl 2-formyl-1-naphthamides

Atroposelective olefination of axially chiral N,N-dialkyl 2-formyl-1-naphthamides with chiral ligand-derived stable arsonium ylides proceeded in a kinetic resolution manner. The (E)-olefin products were obtained in excellent chemical yields and in up to 88:12 diastereoselectivity. Effects of the amide alkyl groups, metal counter ions and solvents on the diastereoselectivity were investigated.