Asymmetric aminocarbonylation of iodoalkenes in the presence of a-phenylethylamine as an N-nucleophile

Mikle, Gábor and Boros, Borbála and Kollár, László (2017) Asymmetric aminocarbonylation of iodoalkenes in the presence of a-phenylethylamine as an N-nucleophile. Tetrahedron: Asymmetry, 28. pp. 1733-1738. ISSN 0957-4166

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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, 3b-hydroxy-20-iodopregna-5,20-diene and 3b-hydroxy-12-iodo-5a,25R-spirost-11-ene were aminocarbonylated with enantiomerically pure and racemic a-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 a-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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