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Exceptional Stereoselectivity in the Synthesis of 1,3,4-Trisubstituted 4-Carboxy β-Lactam Derivatives from Amino Acids

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journal contribution
posted on 12.04.2007, 00:00 by Paula Pérez-Faginas, Fran O'Reilly, Aisling O'Byrne, Carlos García-Aparicio, Mercedes Martín-Martínez, M. Jesús Pérez de Vega, M. Teresa García-López, Rosario González-Muñiz
The base-promoted cyclization of optically pure N-(p-methoxybenzyl)-N-(2-chloro)propionyl amino acid derivatives resulted in a diastereo- and enantioselective approach to valuable 1,3,4,4-tetrasubstituted β-lactams. The stereochemical outcome of the reaction is exclusively governed by the configuration of the N-(2-chloro)propionyl moiety.