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. (C) 2000 Elsevier Science Ltd. All rights reserved.
Stereoselective synthesis of a new enantiopure tricyclic beta-lactam derivative via a tricarbonyl(eta(6)-arene)chromium(0) complex / P. Del Buttero, C. Baldoli, G. Molteni, T. Pilati. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 11:9(2000), pp. 1927-1941. [10.1016/S0957-4166(00)00137-3]
Stereoselective synthesis of a new enantiopure tricyclic beta-lactam derivative via a tricarbonyl(eta(6)-arene)chromium(0) complex
G. Molteni;
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. (C) 2000 Elsevier Science Ltd. All rights reserved.
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