Alkylation of amino acids and glutathione in water by o-quinone methide. Reactivity and selectivity
E Modica, R Zanaletti, M Freccero…
Index: Modica; Zanaletti; Freccero; Mella Journal of Organic Chemistry, 2001 , vol. 66, # 1 p. 41 - 52
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Citation Number: 140
Abstract
o-Quinone methide (1) has been produced in water both thermally and photochemically from (2-hydroxybenzyl) trimethylammonium iodide (2). Michael addition reactions of 1 to various amines, and sulfides, including amino acids and glutathione have been carried out, obtaining alkylated adducts (3-16) in fairly good to quantitative yields. The reaction rate and selectivity of 1 toward nitrogen and sulfur nucleophiles, in competition with the hydration ...
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