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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
Author to whom correspondence should be addressed.
Academic Editors: M. Graça P. M. S. Neves and Gianfranco Favi
Molecules 2020, 25(13), 2978; (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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