The tricyclic beta-lactam 5 has been synthesized both in racemic and enantiopure form starting from the enantiomerically pure tricarbonylchromium(0) complex 1. The synthetic sequence involves the stereoselective [2+2] cycloaddition of 1 with acetoxyacetylketene, followed by intramolecular aromatic nucleophilic substitution of the fluorine atom. Mechanistic pathways leading to 5 are discussed.
Stereoselective synthesis of a new enantiopure tricyclic b-lactam derivative via a tricarbonyl(h6-arene)chromium(0) complex
Baldoli Clara;Pilati Tullio
2000
Abstract
The tricyclic beta-lactam 5 has been synthesized both in racemic and enantiopure form starting from the enantiomerically pure tricarbonylchromium(0) complex 1. The synthetic sequence involves the stereoselective [2+2] cycloaddition of 1 with acetoxyacetylketene, followed by intramolecular aromatic nucleophilic substitution of the fluorine atom. Mechanistic pathways leading to 5 are discussed.File in questo prodotto:
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Descrizione: Stereoselective synthesis of a new enantiopure tricyclic beta-lactam derivative via a tricarbonyl(eta(6)-arene)chromium(0) complex
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