6533b86ffe1ef96bd12cddc8

RESEARCH PRODUCT

Synthesis of densely functionalized cispentacin derivatives through selective aziridination and aziridine opening reactions: Orthogonally protected di- and triaminocyclopentanecarboxylates

Loránd KissMelinda NonnMelinda NonnReijo SillanpääFerenc FülöpFerenc FülöpEnikő Forró

subject

chemistry.chemical_classificationDouble bondBicyclic moleculeStereochemistryOrganic ChemistryRegioselectivityAziridineRing (chemistry)Biochemistrychemistry.chemical_compoundchemistryNucleophileDrug DiscoveryStereoselectivityEnantiomerta116

description

A novel substrate-directed synthetic route to a series of highly functionalized, orthogonally protected di- or triaminocyclopentanecarboxylate derivatives with multiple chiral centres from an unsaturated bicyclic β-lactam has been accomplished by applying stereoselective ring C–C double bond aziridination with chloramine-T and phenyltrimethylammonium tribromide, followed by regioselective aziridine opening with different N,O nucleophiles and hydrides. The functionalization strategy was successfully extended for access to enantiomerically pure orthogonally protected triaminocarboxylates.

yearjournalcountryeditionlanguage
2014-11-01Tetrahedron
10.1016/j.tet.2014.09.071https://doi.org/10.1016/j.tet.2014.09.071