Lithium alkylamide catalyzed addition reactions of alkylamines to vinyl monomers, 1. Selective formation of N-α-methylbenzyl-4-vinylphenethylamine

The lithium alkylamide catalyzed addition reaction of α-methylbenzylamine ( 1 ) with styrene was found to produce selectively N-phenethyl-α-methylbenzylamine ( 3 ). Under the same reaction conditions, addition of (S)-α-methylbenzylamine ( 1 ′) to 1,4-divinylbenzene ( 5 ) takes place selectively leading to the optically active novel styrene derivative, (S)-N-α-methylbenzyl-4-vinylphenethylamine ( 6 ), in a one-step reaction. The specific rotation was found to be [α]⁴_D = ?70,1° (c = 1,61 g/dl, in methanol). The following Q, e-values and the monomer reactivity rations of 6 (M₁) and styrene ( M ₂) were obtained: Q₁ = 1,59, e₁ = ?1,28; r₁ = 0,86, r₂ = 0,92.