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Inversion of Configuration of (S)-β-Hydroxy-γ-butyrolactone with Total Retention of the Enantiomeric Purity

✍ Scribed by Francesco De Angelis; Enrico De Fusco; Paola Desiderio; Fabio Giannessi; Fabrizio Piccirilli; Maria Ornella Tinti

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 275 KB
Volume: 1999
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199911)1999:11<2705::aid-ejoc2705>3.0.co;2-4

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✦ Synopsis

In this paper we report the inversion of configuration of (S)-the production of (R)-GABOB and (R)-carnitine, among other biologically active compounds, from a D-hexose source, or, β-hydroxy-γ-butyrolactone [(S)-1] to its (R) enantiomer (R)-1, with total retention of the enantiomeric purity, by a four-step alternatively, from the industrial waste compound (S)carnitine. During the reaction sequence, the intermediate β-procedure. The (R)-β-hydroxy-γ-butyrolactone [(R)-1] was thus synthetized with an overall chemical yield of 47% and lactone 4 is also prepared, which is now under investigation as a chiral synthon for new synthetic applications. > 97% ee. This transformation opens an economic route to [a]

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