## Abstract The target compounds are prepared with anti‐ or syn‐selectivity using D‐ or L‐proline as a catalyst, respectively.
Enantioselective synthesis of (R)-(+)-α-lipoic acid via proline-catalyzed sequential α-aminoxylation and HWE olefination of aldehyde
✍ Scribed by Sharad P. Panchgalle; Ganesh F. Jogdand; Subhash P. Chavan; Uttam R. Kalkote
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- French
- Weight
- 291 KB
- Volume
- 51
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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.
📜 SIMILAR VOLUMES
The enantioselective total synthesis of (+)-patulolide C isolated from Penicillium urticae has been achieved from commercially available 9-decen-1-ol. Jacobsen's kinetic resolution and sequential a-aminooxylation and Horner-Wadsworth-Emmons (HWE) olefination followed by Yamaguchi lactonization are u
## Abstract The sequence starts with Jacobsen′s kinetic resolution.
A short and high yielding enantioselective synthesis of (À)-bestatin, a naturally occurring aminopeptidase inhibitor, is described via L-proline-catalyzed asymmetric a-amination of 3-phenylpropionaldehyde as the key reaction. The methodology also involves a Pd-catalyzed intramolecular cyclization of
The asymmetric synthesis of methyl (S)-6,8-dihydroxyoctanoate ( ) and (S)-6,8-dimethylsulfonyloxyoctane-1-carboxylic acid (13), key precursors to R-(+)-a-lipoic acid (6) is described using OsO 4 -catalyzed asymmetric dihydroxylation and Ru-catalyzed asymmetric hydrogenation, respectively, as the key