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

Nonn, Melinda and Kiss, Loránd and Forró, Enikő and Sillanpaa, Reijo and Fülöp, Ferenc (2014) Synthesis of densely functionalized cispentacin derivatives through selective aziridination and aziridine opening reactions: orthogonally protected di- and triaminocyclopentanecarboxylates. Tetrahedron, 70. pp. 8511-8519. ISSN 0040-4020

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Abstract

A novel substrate-directed synthetic route to a series of highly functionalized, orthogonally protected dior triaminocyclopentanecarboxylate derivatives with multiple chiral centres from an unsaturated bicyclic b-lactam has been accomplished by applying stereoselective ring CeC 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.

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