Enantioselective synthesis of indole derivatives

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Indole, and structures derived from it, are a component of many natural substances, such as the amino acid tryptophan. A new catalytic reaction produces cyclopenta[b]indoles -- frameworks made of three rings that are joined at the edges -- very selectively and with the desired spatial structure. The rates of the different steps of the reaction play a critical role.
Indole, and structures derived from it, are a component of many natural substances, such as the amino acid tryptophan. A new catalytic reaction produces cyclopenta[b]indoles -- frameworks made of three rings that are joined at the edges -- very selectively and with the desired spatial structure. As a research team reports in the journal Angewandte Chemie, the rates of the different steps of the reaction play a critical role.

Indole derivates are widely distributed in nature; they are part of serotonin and melatonin, as well as many alkaloids -- some of which are used as drugs, for example, as treatments for Parkinson's disease. Indole is an aromatic six-membered ring fused to a five-membered ring along one edge. The five-membered ring has a double bond and a nitrogen atom. The basic indole framework can be equipped with a variety of side groups or bound to additional rings. Indole and many indole derivatives can be made by an indole synthesis reaction developed by and named after Emil Fischer (acid-assisted condensation of ketones with phenyl hydrazines).

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