Synthesis of chiral α-ethylphenylamine salts of tartaric acid and novel application to cyanosilylation of prochiral ketones

Abstract

Chiral α-ethylphenylamine tartaric acid salts were synthesized from α-ethylphenylamine by direct reaction with chiral tartaric acid. The crystal structure of S-(−)-α-ethylphenylamine-(2R,3R)-(−)-dihydroxybutanedioic acid was determined. The crystal is monoclinic, of space group P21/n , with a = 6.331(5) A, b = 14.209(11) A, c = 7.495(6) A, α = 90.00o, β = 107.000(13)o, γ = 90.00o, λ = 0.7103 Ǻ, V = 644.7(9), Z = 2, D c = 1.397 g/cm3, M r = 271.27 and F(000) = 288, R = 0.0477, and ωR = 0.0838 for 1388 observed reflections with I > 2σ(I). We then used the chiral α-ethylphenylamine tartaric acid salts as catalysts in the cyanosilylation of prochiral ketones, and moderate conversions were obtained. The crystal structure of a chiral α-phenylethylamine tartaric acid salt, and novel application to the cyanosilylation of prochiral ketones Chiral α-ethylphenylamine tartaric acid salts were synthesized from α-ethylphenylamine by direct reaction with chiral tartaric acid. The crystal structure of S-(−)-α-ethylphenylamine-(2R,3R)-(−)-dihydrobutanedioic acid was determined. When the chiral α-ethylphenylamine tartaric acid salts were used as catalysts in the cyanosilylation of prochiral ketones, moderate conversions were obtained