ISSN:
1434-193X
Keywords:
Asymmetric synthesis
;
Chiral synthons
;
Configuration inversion
;
Hydroxy lactones
;
Lactones
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
In this paper we report the inversion of configuration of (S)-β-hydroxy-γ-butyrolactone [(S)-1] to its (R) enantiomer (R)-1, with total retention of the enantiomeric purity, by a four-step procedure. The (R)-β-hydroxy-γ-butyrolactone [(R)-1] was thus synthetized with an overall chemical yield of 47% and 〉 97% ee. This transformation opens an economic route to the production of (R)-GABOB and (R)-carnitine, among other biologically active compounds, from a D-hexose source, or, alternatively, from the industrial waste compound (S)-carnitine. During the reaction sequence, the intermediate β-lactone 4 is also prepared, which is now under investigation as a chiral synthon for new synthetic applications.
Type of Medium:
Electronic Resource
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