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Chloromethylaluminum 2 (2-propenyl)anilide - a convenient reagent for the conversion of lactones into protected hydroxy acids

✍ Scribed by Anthony G.M. Barrett; Dashyant Dhanak

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
196 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

The title reagent reacts with 7 and 6 lactones to provide hydroxy amides which can be easily converted into protected N-acyl indoles.

Mild saponification provides indole and the protected hydroxy acid.

Several years ago, Weinreb et reported1 a mild method for the conversion of esters into amides. This involved reaction of the ester with dialkylaluminum amides derived from

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EEDQ has been utilized as a convenient reagent for the selective protection of the hydroxy group of 2hydroxycarboxylic acids. In the presence of an appropriate amine nucleophile, EEDQ has also been utilized as a reagent for the derivatization of both of the hydroxy and carboxylic acid group of 2-hyd