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...
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| Published in | Tetrahedron: asymmetry Vol. 25; no. 23; pp. 1527 - 1531 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
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Elsevier Ltd
15.12.2014
Elsevier |
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| Abstract | [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. |
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| AbstractList | A palladium-catalysed aminocarbonylation of a steroidal iodoalkene (17-iodo-5 alpha-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 5 alpha-reductase inhibitors. Both epimers of the monocarboxamide and those of the dicarboxamide, formed with moderate diastereoselectivity, were isolated and fully characterised. (C) 2014 Elsevier Ltd. All rights reserved. [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. |
| Author | Boros, Borbála Kollár, László Mikle, Gábor |
| Author_xml | – sequence: 1 givenname: Gábor surname: Mikle fullname: Mikle, Gábor organization: Department of Inorganic Chemistry, University of Pécs and Szentágothai Research Centre, PO Box 266, H-7624 Pécs, Hungary – sequence: 2 givenname: Borbála surname: Boros fullname: Boros, Borbála organization: Department of Analytical and Environmental Chemistry, University of Pécs, Ifjúság u. 6., H-7624 Pécs, Hungary – sequence: 3 givenname: László surname: Kollár fullname: Kollár, László email: kollar@gamma.ttk.pte.hu organization: Department of Inorganic Chemistry, University of Pécs and Szentágothai Research Centre, PO Box 266, H-7624 Pécs, Hungary |
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| CitedBy_id | crossref_primary_10_1002_slct_202002093 crossref_primary_10_1016_j_mcat_2017_10_031 crossref_primary_10_1016_j_tet_2021_132050 crossref_primary_10_1016_j_tetasy_2016_03_010 crossref_primary_10_1016_j_tetasy_2017_10_012 |
| Cites_doi | 10.1002/chem.201000090 10.1016/j.tetlet.2013.02.108 10.1016/j.steroids.2006.05.019 10.1016/j.steroids.2007.04.004 10.1002/anie.200900013 10.1016/S0040-4020(01)85237-6 10.1039/c39870000904 10.2174/1385272023373699 10.1081/SCC-100000521 10.1016/S0040-4039(00)81721-9 10.1021/om00012a029 10.1016/S0022-1139(99)00175-X 10.1016/S0040-4039(00)83920-9 10.1016/S0020-1693(98)00366-1 10.1016/0039-128X(95)00120-F 10.1039/jr9620000470 10.1021/ja00297a033 10.1021/om00045a012 10.1016/S0040-4039(98)01054-5 10.1021/jm00165a009 10.1080/00397919808006865 |
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A palladium-catalysed aminocarbonylation of a steroidal iodoalkene (17-iodo-5α-androst-16-ene) model compound with... A palladium-catalysed aminocarbonylation of a steroidal iodoalkene (17-iodo-5 alpha-androst-16-ene) model compound with 2,2'-diamino-1,1'-binaphthalene as an... |
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| Title | Diastereoselective aminocarbonylation of a steroidal iodoalkene with 2,2′-diamino-1,1′-binaphthalene in palladium-catalysed reactions |
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