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) Å, b = 14.209(11) Å, c = 7.495(6) Å, 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.
Graphical Abstract
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
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Mei, L., Jie, S. & Ying, J. Synthesis of chiral α-ethylphenylamine salts of tartaric acid and novel application to cyanosilylation of prochiral ketones. Res Chem Intermed 36, 227–236 (2010). https://doi.org/10.1007/s11164-010-0132-7
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DOI: https://doi.org/10.1007/s11164-010-0132-7