- A chemoenzymatic approach to the synthesis of enantiomerically pure aza analogues of paraconic acid methyl ester and both enantiomers of methyl β-proline
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Enantiopure methyl esters of 1-alkyl-5-oxo-3-pyrrolidinecarboxylic acids were obtained by enzymatic resolution of the corresponding chiral racemic mixtures. A particularly favourable interaction, also supported by molecular mechanics calculations, was observed between the 1-benzyl derivative and α-chymotrypsin, for which the enantiomeric ratio, E, exceeded 200. The absolute configurations of the lactams were determined by means of CD spectroscopy. From the resulting enantiomerically pure (99% e.e.) (S)-(+)-1-benzyl-3-pyrrolidinecarboxylic acid and methyl (R)-(-)-1-benzyl-3-pyrrolidinecarboxylate, the methyl esters of (+) and (-)-β-proline were synthesised in 99% e.e. and 18 and 22% overall yield, respectively.
- Felluga, Fulvia,Pitacco, Giuliana,Prodan, Massimo,Pricl, Sabrina,Visintin, Marco,Valentin, Ennio
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p. 3241 - 3249
(2007/10/03)
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- Phenyloxazoles and phenylthiazoles as benzamide bioisosteres: Synthesis and dopamine receptor binding profiles
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Conformationally restricted benzamide bioisosteres were investigated when the aminomethylpyrrolidine derivative 4o proved D3 as well as D4 binding properties which were comparable to those of the atypical neuroleptics sulpiride and clozapine, respectively. (C) 2000 Elsevier Science Ltd.
- Einsiedel, Juergen,Thomas, Christoph,Huebner, Harald,Gmeiner, Peter
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p. 2041 - 2044
(2007/10/03)
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