Planar chiral [2.2]paracyclophane-based phosphine-phenol catalysts: application to the aza-Morita-Baylis-Hillman reaction of N-sulfonated imines with various vinyl ketones

Abstract

Several planar chiral [2.2]paracyclophane-based phosphine-phenol catalysts were prepared and applied to the aza-Morita-Baylis-Hillman reaction of aldimines with vinyl ketones. The pseudo-ortho-substituted aryl[2.2]paracyclophanol, in which the phosphino group was located at the meta-position of the aryl group, showed an exceptionally high reactivity and good enantioselectivity for the reaction of N-tosylated aldimines with various alkyl or aryl vinyl ketones.