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A short enantioselective synthesis of (−)-bestatin via l-proline-catalyzed α-amination of an aldehyde

✍ Scribed by Shyla George; Gurunath S. Suryavanshi; Arumugam Sudalai

Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
151 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 an allylic acetate giving a trans-oxazoline in a highly diastereoselective manner (dr > 14:1).

📜 SIMILAR VOLUMES

Enantioselective synthesis of (R)-(+)-α-
Enantioselective synthesis of (R)-(+)-α-lipoic acid via proline-catalyzed sequential α-aminoxylation and HWE olefination of aldehyde
✍ Sharad P. Panchgalle; Ganesh F. Jogdand; Subhash P. Chavan; Uttam R. Kalkote 📂 Article 📅 2010 🏛 Elsevier Science 🌐 French ⚖ 291 KB

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.