20.500.12556/RUL-133821 Stereodivergent synthesis of camphor-derived diamines and their application as thiourea organocatalysts A series of 18 regio- and stereo-chemically diverse chiral non-racemic 1,2-, 1,3-, and 1,4-diamines have been synthesized from commercial (1S)-(+)-ketopinic acid and (1S)-(+)-10-camphorsulfonic acid. The structures of the diamines are all based on the D-(+)-camphor scaffold and feature isomeric diversity in terms of regioisomeric attachment of the primary and the tertiary amine function and the exo/endo-isomerism. Diamines were transformed into the corresponding noncovalent bifunctional thiourea organocatalysts, which have been evaluated for catalytic activity in the conjugative addition of 1,3-dicarbonyl nucleophiles (dimethyl malonate, acetylacetone, and dibenzoylmethane) to trans-β-nitrostyrene. The highest enantioselectivity was achieved in the reaction with acetylacetone as nucleophile using endo-1,3-diamine derived catalyst 52 (91.5:8.5 er). All new organocatalysts 48–63 have been fully characterized. The structures and the absolute configurations of eight intermediates and thiourea derivative 52 were also determined by X-ray diffraction. (+)-camphor diamines thiourea bifunctional organocatalysts asymmetric synthesis (+)-kafra diamini tiosečnina bifunkcionalni organokatalizatorji asimetrična sinteza true false true Angleški jezik Slovenski jezik Članek v reviji 2021-12-16 11:53:09 2021-12-16 11:53:10 2022-09-13 03:52:44 0000-00-00 00:00:00 2020 0 0 22 str. iss. 13, art. 2978 Vol. 25 Jul. 2020 0000-00-00 Zaloznikova Objavljeno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 547.415.1 1420-3049 10.3390/molecules25132978 24479491 RAZ_Ricko_Sebastijan_2020.pdf RAZ_Ricko_Sebastijan_2020.pdf 1 152DEC3206D04C8E578B2ADD807684F2 b4e7e87ea2ac0952189835a58967cdc8c613acc9e609094195001cafa3f9f7a5 7aa3bda6-5e5e-11ec-abdb-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=152177 https://www.mdpi.com/1420-3049/25/13/2978 0 3b5abf8f-5e5e-11ec-abdb-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=152175 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0