An enantioselective synthesis of R-(+)-?-lipoic acid
β Scribed by Page, Philip C. Bulman; Rayner, Christopher M.; Sutherland, Ian O.
- Book ID
- 111890883
- Publisher
- Royal Society of Chemistry
- Year
- 1990
- Weight
- 562 KB
- Volume
- 6
- Category
- Article
- ISSN
- 1472-7781
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## Abstract The fungal metabolite (__R__)β(+)βpulvilloric acid [(+)β1] was synthesized for the first time. Reaction of the Grignard reagent of 5 with 2βpentyloxirane (__S__)β(β)β4 in the presence of 1,5βcyclooctadienecopper(I) chloride as the catalyst led to (__S__)β(+)β6. The enantiomer (__S__)β(β
An efficient enantioselective synthesis of (R)-(+)-a-lipoic acid is described, in high optical purity (>97% ee), using L-proline-catalyzed sequential a-aminoxylation and Horner-Wadsworth-Emmons olefination of aldehyde as the key step.