Chiral Auxiliary-Directed Site-Selective Deprotonation of the Cubane Skeleton
Hiyori Takebe, Nana Yoshino, Yukako Shimada, Craig M. Williams, Seijiro Matsubara
Abstract
The first diastereoselective synthesis of trisubstituted cubanes was achieved using a chiral auxiliary. To establish chirality within the cubane skeleton, at least three substituents must be introduced at the appropriate positions. Ready conversion of cubane carboxylic acid to a chiral amide followed by sequential ortho -selective deprotonations and electrophilic trapping afforded the corresponding 1,2,3-trisubstituted cubanes with high diastereoselectivity. This route opens new possibilities for the preparation of enantio-enriched cubanes.
Topics & Concepts
ChemistryCubaneElectrophileDeprotonationStereochemistryChirality (physics)AmideSkeleton (computer programming)Combinatorial chemistryMoleculeCatalysisOrganic chemistryIonComputer scienceQuantum mechanicsPhysicsQuarkProgramming languageChiral symmetry breakingNambu–Jona-Lasinio modelAsymmetric Synthesis and CatalysisCoordination Chemistry and OrganometallicsSynthetic Organic Chemistry Methods