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Open AccessArticle

Stereodivergent Synthesis of Camphor-Derived Diamines and Their Application as Thiourea Organocatalysts

Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, 1000 Ljubljana, Slovenia
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Academic Editors: M. Graça P. M. S. Neves and Gianfranco Favi
Molecules 2020, 25(13), 2978; https://doi.org/10.3390/molecules25132978 (registering DOI)
Received: 5 June 2020 / Revised: 26 June 2020 / Accepted: 27 June 2020 / Published: 29 June 2020
(This article belongs to the Special Issue 25th Anniversary of Molecules—Recent Advances in Organic Synthesis)
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 4863 have been fully characterized. The structures and the absolute configurations of eight intermediates and thiourea derivative 52 were also determined by X-ray diffraction. View Full-Text
Keywords: (+)-camphor; diamines; thiourea; bifunctional organocatalysts; asymmetric synthesis (+)-camphor; diamines; thiourea; bifunctional organocatalysts; asymmetric synthesis
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MDPI and ACS Style

Ričko, S.; Požgan, F.; Štefane, B.; Svete, J.; Golobič, A.; Grošelj, U. Stereodivergent Synthesis of Camphor-Derived Diamines and Their Application as Thiourea Organocatalysts. Molecules 2020, 25, 2978.

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