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

[Display omitted] A palladium-catalysed aminocarbonylation of a steroidal iodoalkene (17-iodo-5α-androst-16-ene) model compound with 2,2′-diamino-1,1′-binaphthalene as an N-nucleophile was carried out. The combination of a steroidal skeleton possessing central elements of chirality and a binaphthyl...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron: asymmetry Vol. 25; no. 23; pp. 1527 - 1531
Main Authors Mikle, Gábor, Boros, Borbála, Kollár, László
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.12.2014
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
FACILE SYNTHESIS
CARBONYLATION
ARYL HALIDES
RESOLUTION
COMPLEXES
Online AccessGet full text

Cover

More Information
Summary:[Display omitted] A palladium-catalysed aminocarbonylation of a steroidal iodoalkene (17-iodo-5α-androst-16-ene) model compound with 2,2′-diamino-1,1′-binaphthalene as an N-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 5α-reductase inhibitors. Both epimers of the monocarboxamide and those of the dicarboxamide, formed with moderate diastereoselectivity, were isolated and fully characterised.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2014.10.013