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Theoretical study of ester enolate-imine condensation route to ?-lactams

✍ Scribed by Del R�o, E.; L�pez, R.; Men�ndez, M. I.; Sordo, T. L.; Ruiz-L�pez, M. F.

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
356 KB
Volume
19
Category
Article
ISSN
0192-8651

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✦ Synopsis

The condensation reaction of the enolate of methyl acetate with formaldimine to afford a ␤-lactam was studied using the MP2-FCr6-31qG* level of theory taking into account the electrostatic effect of the solvent by means of a self-consistent reaction field continuum model. The reaction is a stepwise process with three main steps: the formation of the C3 C4 bond, the closure of the ␤-lactam ring, and the elimination of the methoxide ion. The formation of the C3 C4 bond is rate determining and according to our calculations is not a reversible step.

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## Abstract In the presence of NaN(Tms)~2~, esters of type (I) and (IX) rearrange to amino acids like (II) and (X) with moderate to high diastereoselectivity.