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Synthesis and spectroscopic studies of optically active n-acetyl butenoates and n-acetyl-2-alkyl-pyrrolin-4-ones

โœ Scribed by Efstathios Gavrielatos; Giorgos Athanasellis; Olga Igglessi-Markopoulou


Publisher
Journal of Heterocyclic Chemistry
Year
2002
Tongue
English
Weight
43 KB
Volume
39
Category
Article
ISSN
0022-152X

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โœฆ Synopsis


Abstract

The synthesis of a series of optically active Nโ€acetyl butenoates 3โ€“5 is described using a facile methodology. These butenoates undergo cyclization to the corresponding Nโ€acetylโ€2โ€alkylโ€pyrrolinโ€4โ€ones 6,7 retaining their stereochemical integrity. The structure of the newly synthesized compounds has been elucidated through ^1^Hโ€^13^C NMR, IR spectroscopy and their enantiomeric excesses have been measured by chiral HPLC analysis.


๐Ÿ“œ SIMILAR VOLUMES


Synthesis and NMR spectroscopic studies
โœ Margarita Petroliagi; Olga Igglessi-Markopoulou ๐Ÿ“‚ Article ๐Ÿ“… 2001 ๐Ÿ› Journal of Heterocyclic Chemistry ๐ŸŒ English โš– 53 KB

## Abstract An efficient method for the preparation of optically active derivatives of ฮณโ€aminoโ€butenoic acids and their cyclic derivatives, 2โ€aminoโ€pyrrolinโ€4โ€ones, from ฮฑโ€amino acids is described. Partial racemization accompanies the formation of initial unsaturated ฮณโ€aminoโ€ฮฒโ€hydroxy esters **5โ€“8*

Synthesis and Spectroscopic Characteriza
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Title compound 1 was synthesized by a published route which had to be modified (seven steps from readily obtainable starting materials). Characterization of 1 was achieved by spectroscopic means (FAB-MS, ' H-NMR, including 2D-COSY). Furthermore, commercially available reference material purchased fo