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


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-?-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.

SUBMITTER: Ricko S 

PROVIDER: S-EPMC7412124 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature

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

Ričko Sebastijan S   Požgan Franc F   Štefane Bogdan B   Svete Jurij J   Golobič Amalija A   Grošelj Uroš U  

Molecules (Basel, Switzerland) 20200629 13


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 (1<i>S</i>)-(+)-ketopinic acid and (1<i>S</i>)-(+)-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 <i>exo/endo</i>-isomerism. Diamines were transformed into the corresponding noncovalent  ...[more]

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