Asymmetric Synthesis of ( R )-Antofine and ( R )-Cryptopleurine via Proline-Catalyzed Sequential α-Aminoxylation and Horner−Wadsworth−Emmons Olefination of Aldehyde
✍ Scribed by Cui, Mingbo; Song, Hongjian; Feng, Anzheng; Wang, Ziwen; Wang, Qingmin
- Book ID
- 119993187
- Publisher
- American Chemical Society
- Year
- 2010
- Tongue
- English
- Weight
- 784 KB
- Volume
- 75
- Category
- Article
- ISSN
- 0022-3263
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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 target compounds are prepared with anti‐ or syn‐selectivity using D‐ or L‐proline as a catalyst, respectively.
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.
## Abstract The sequence starts with Jacobsen′s kinetic resolution.