alpha-Carboxy-6-nitroveratryl: A Photolabile Protecting Group for Carboxylic Acids

作者:Russell Alexander G; Ragoussi Maria Eleni; Ramalho Rui; Wharton Christopher W; Carteau David; Bassani Dario M*; Snaith John S
来源:Journal of Organic Chemistry, 2010, 75(13): 4648-4651.
DOI:10.1021/jo100783v

摘要

The synthesis of a new photolabile protecting group for carboxylic acids, alpha-carboxy-6-nitroveratryl (alpha CNV), is described. Bromide 3, prepared in four steps from 3,4-dimethoxyphenylacetic acid, was used to alkylate carboxylic acids under mild conditions in good yield. Palladium-catalyzed deallylation afforded the acids 4a-h, which underwent rapid and quantitative photolysis at wavelengths longer than 300 nm to liberate the carboxylic acid in good to quantitative yield. The rate of photolysis and quantum yield were determined to be 325 s(-1) and 0.17.

  • 出版日期2010-7-2