Diastereo- and enantioselective synthesis of orthogonally protected 2,4-diaminocyclopentanecarboxylates: a flip from beta-amino- to beta,gamma-diaminocarboxylates.
Conformationally restricted, orthogonally protected 2,4-diaminocarboxylates with a cyclopentane skeleton were efficiently synthesized from beta-lactam 6, the syntheses involving strategies of diastereoselective epoxidation of the beta-lactam and the corresponding monoprotected amino esters with opposite selectivities followed by regioselective opening of the oxirane ring with sodium azide. The enantiomers were also prepared. This new class of compounds can be regarded not only as conformationally constrained beta,gamma-diamino acid derivatives but also as potential functionalized carbocyclic nucleoside precursors.
Kiss
Lorand
L
Institute of Pharmaceutical Chemistry and Research Group of Stereochemistry of the Hungarian Academy of Sciences, University of Szeged, H-6720 Szeged, Eötvös utca 6, Hungary.
Forró
Enikó
E
Sillanpää
Reijo
R
Fülöp
Ferenc
F
D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D005027:Ethylene Oxide / Q000031:analogs & derivatives / Q000737:chemistry; D008968:Molecular Conformation; D019810:Sodium Azide / Q000737:chemistry; D013237:Stereoisomerism; D047090:beta-Lactams / Q000737:chemistry
D002264:Carboxylic Acids; D003517:Cyclopentanes; D004952:Esters; D047090:beta-Lactams; D019810:Sodium Azide; D005027:Ethylene Oxide