Synthesis and spectroscopic studies of optically active n-acetyl butenoates and n-acetyl-2-alkyl-pyrrolin-4-ones
โ 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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โฆ Synopsis
Abstract
The synthesis of a series of optically active Nโacetyl butenoates 3โ5 is described using a facile methodology. These butenoates undergo cyclization to the corresponding Nโacetylโ2โalkylโpyrrolinโ4โones 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.
๐ SIMILAR VOLUMES
## Abstract An efficient method for the preparation of optically active derivatives of ฮณโaminoโbutenoic acids and their cyclic derivatives, 2โaminoโpyrrolinโ4โones, from ฮฑโamino acids is described. Partial racemization accompanies the formation of initial unsaturated ฮณโaminoโฮฒโhydroxy esters **5โ8*
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