New synthetic technology for efficient construction of alpha-hydroxy-beta-amino amides via the Passerini reaction

Authors
Semple, JE Owens, TD Nguyen, K Levy, OE
Citation
Je. Semple et al., New synthetic technology for efficient construction of alpha-hydroxy-beta-amino amides via the Passerini reaction, ORG LETT, 2(18), 2000, pp. 2769-2772
Citations number
48
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
18
Year of publication
2000
Pages
2769 - 2772
Database
ISI
SICI code
1523-7060(20000907)2:18<2769:NSTFEC>2.0.ZU;2-B
Abstract
The Passerini reaction of N-protected amino aldehydes, isonitriles, and TFA using pyridine-type bases proceeds under mild conditions and directly affo rds alpha-hydroxy-beta-amino amide derivatives in moderate to high yields. These adducts are readily hydrolyzed to alpha-hydroxy-beta-amino carboxylic acids. Application of these key intermediates to concise syntheses of P-1- alpha-ketoamide protease inhibitors is illustrated.