Asymmetric aminocarbonylation of iodoalkenes in the presence of α-phenylethylamine as an N-nucleophile |
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Authors: | Gábor Mikle Borbála Boros László Kollár |
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Institution: | 1. Department of Inorganic Chemistry, University of Pécs and Szentágothai Research Centre, H-7624 Pécs, P.O. Box 266, Hungary;2. Department of Analytical and Environmental Chemistry, University of Pécs, H-7624 Pécs, Ifjúság u. 6., Hungary;3. MTA-PTE Research Group for Selective Chemical Syntheses, H-7624 Pécs, Ifjúság u. 6., Hungary |
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Abstract: | Iodoalkenes, such as 2-iodo-bornene, 17-iodoandrost-16-ene, 3-methoxy-17-iodoestra-1,3,5(10),16-ene, 3β-hydroxy-20-iodopregna-5,20-diene and 3β-hydroxy-12-iodo-5α,25R-spirost-11-ene were aminocarbonylated with enantiomerically pure and racemic α-phenylethylamine as the N-nucleophile in the presence of palladium(0) catalysts. Monodentate and bidentate (chiral and achiral) phosphines were used as ligands in the catalytic system. All diastereoisomers of the corresponding carboxamides were characterised as pure stereoisomers using both α-phenylethylamine and iodoalkene in enantiomerically pure form. The diastereoisomers were obtained in moderate to high yields in a chemoselective reaction, i.e., carboxamides due to single carbon monoxide insertion were formed exclusively, with no double CO insertion leading to 2-ketocarboxamides. Diastereoselectivities of the aminocarbonylation were investigated using the N-nucleophile in racemic form by the systematic variation of the catalyst. |
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Keywords: | Corresponding author Tel : +36 72 503600 |
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