Sebastijan Ričko (Avtor), Franc Požgan (Avtor), Bogdan Štefane (Avtor), Jurij Svete (Avtor), Amalija Golobič (Avtor), Uroš Grošelj (Avtor)

Povzetek

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.

Ključne besede

(+)-kafra;diamini;tiosečnina;bifunkcionalni organokatalizatorji;asimetrična sinteza;(+)-camphor;diamines;thiourea;bifunctional organocatalysts;asymmetric synthesis;

Podatki

Jezik: Angleški jezik
Leto izida:
Tipologija: 1.01 - Izvirni znanstveni članek
Organizacija: UL FKKT - Fakulteta za kemijo in kemijsko tehnologijo
UDK: 547.415.1
COBISS: 24479491 Povezava se bo odprla v novem oknu
ISSN: 1420-3049
Št. ogledov: 364
Št. prenosov: 57
Ocena: 0 (0 glasov)
Metapodatki: JSON JSON-RDF JSON-LD TURTLE N-TRIPLES XML RDFA MICRODATA DC-XML DC-RDF RDF

Ostali podatki

Sekundarni jezik: Slovenski jezik
Sekundarne ključne besede: (+)-kafra;diamini;tiosečnina;bifunkcionalni organokatalizatorji;asimetrična sinteza;
Vrsta dela (COBISS): Članek v reviji
Strani: str. 1-22
Letnik: ǂVol. ǂ25
Zvezek: ǂiss. ǂ13
Čas izdaje: Jul. 2020
DOI: 10.3390/molecules25132978
ID: 14110128