New synthetic technology for efficient construction of α-hydroxy-β-amino amides via the Passerini reaction

被引：116

作者：

Semple, JE ^{[1
]}

Owens, TD ^{[1
]}

Nguyen, K ^{[1
]}

Levy, OE ^{[1
]}

机构：

[1] Corvas Int Inc, Dept Med Chem, San Diego, CA 92121 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 18期

关键词：

D O I：

10.1021/ol0061485

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2769 / 2772

页数：4

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