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

Abstract

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.

Keywords

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

Data

Language: English
Year of publishing:
Typology: 1.01 - Original Scientific Article
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
UDC: 547.415.1
COBISS: 24479491 Link will open in a new window
ISSN: 1420-3049
Views: 364
Downloads: 57
Average score: 0 (0 votes)
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Other data

Secondary language: Slovenian
Secondary keywords: (+)-kafra;diamini;tiosečnina;bifunkcionalni organokatalizatorji;asimetrična sinteza;
Type (COBISS): Article
Pages: str. 1-22
Volume: ǂVol. ǂ25
Issue: ǂiss. ǂ13
Chronology: Jul. 2020
DOI: 10.3390/molecules25132978
ID: 14110128