Photochemical cleavage and release of carboxylic acids from alpha-keto amides |
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Authors: | Ma Chicheng Steinmetz Mark G Cheng Qing Jayaraman Vasanthi |
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Affiliation: | Department of Chemistry, Marquette University, Milwaukee, WI 53201-1881, USA. |
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Abstract: | Carboxylate groups incorporated at the position alpha to the keto carbonyl of alpha-keto amides 1 were photochemically cleaved in aqueous media to give carboxylic acids in 70-90% yields with quantum yields of 0.3. The cleavage coproducts were diastereomeric hemiacetals 2. Prompt release of acetate and gamma-aminobutyrate (GABA) in buffer was observed by difference FT-IR spectroscopy upon 355 nm laser flash photolysis. The time-constant for release of GABA was <30 ms. [reaction--see text] |
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