Diastereoselective aminocarbonylation of a steroidal iodoalkene with 2,2’-diamino-1,1’-binaphthalene in palladium-catalysed reactions

Mikle, Gábor and Boros, Borbála and Kollár, László (2014) Diastereoselective aminocarbonylation of a steroidal iodoalkene with 2,2’-diamino-1,1’-binaphthalene in palladium-catalysed reactions. Tetrahedron: Asymmetry, 25 (23). pp. 1527-1531. ISSN 0957-4166

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Abstract

A palladium-catalysed aminocarbonylation of a steroidal iodoalkene (17-iodo-5a-androst-16-ene) model compound with 2,2'-diamino-1,1'-binaphthalene as anN-nucleophile was carried out. The combination of a steroidal skeleton possessing central elements of chirality and a binaphthyl moiety with axial chirality was carried out resulting in a novel type of steroidal carboxamides. The binaphthalene—steroid conjugates are potential 5a-reductase inhibitors. Both epimers of the monocarboxamide and those of the dicarboxamide, formed with moderate diastereoselectivity, were isolated and fully characterised.

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