Palladium-Catalyzed Generation of ortho-Quinone Methides. A Three-Component Synthesis of L-Shaped Dimeric Steroidal Scaffolds

0539866 - ÚFCH JH 2022 RIV US eng J - Journal Article
Mayorquín-Torres, M. C. - Navarro-Huerta, A. - Maldonado-Domínguez, Mauricio - Flores-Álamo, M. - Rodríguez-Molina, B. - Iglesias-Arteaga, M. A.
Palladium-Catalyzed Generation of ortho-Quinone Methides. A Three-Component Synthesis of L-Shaped Dimeric Steroidal Scaffolds.
Journal of Organic Chemistry. Roč. 86, č. 5 (2021), s. 4112-4120. ISSN 0022-3263. E-ISSN 1520-6904
Grant - others:Ga MŠk(CZ) LM2015070
Institutional support: RVO:61388955
Keywords : Crystals * Oligomers * Molecules
OECD category: Physical chemistry
Impact factor: 4.198, year: 2021
Method of publishing: Limited access

A series of hybrid dimers having orthogonal steroidal cores bridged by a chroman ketal moiety were obtained by Pd-catalyzed three-component reactions of steroid alkynols, 2-formylestradiol 17-monoacetate, and methyl orthoformate, via ortho-quinone methide intermediates. One of the obtained L-shaped scaffolds showed an inefficient crystal packing featuring large channels within the crystal array. Monte Carlo simulations indicate that these voids preferentially allocate n-hexane, opening the way to explore further applications of similar organic crystalline materials as selective hosts for small molecules.
Permanent Link: http://hdl.handle.net/11104/0317564