New Synthetic Technology for Efficient Construction of α-Hydroxy-β-amino Amides via the Passerini Reaction1
Organic Letters2000Vol. 2(18), pp. 2769–2772
Citations Over TimeTop 10% of 2000 papers
Abstract
[reaction: see text] The Passerini reaction of N-protected amino aldehydes, isonitriles, and TFA using pyridine-type bases proceeds under mild conditions and directly affords 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.
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