Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5264887 | Tetrahedron Letters | 2012 | 4 Pages |
Abstract
An efficient method for the preparation of 4-oxo-4,5,6,7-tetrahydroindoles was successfully applied to the synthesis of N-substituted 7-oxo-4,5,6,7-tetrahydroindoles for the first time. Both isomers where converted into their corresponding 4- and 7-oxoindoles in good yields utilizing a novel aromatization protocol. Based on the impurity profile obtained, however, different mechanisms for the formation of the 4- and 7-oxo-4,5,6,7-tetrahydroindole derivatives are discussed. In addition, the reaction sequences appear to be stereospecific allowing for the direct introduction of a chiral center α to the nitrogen and preparation of enantiomerically enriched products.
Related Topics
Physical Sciences and Engineering
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Authors
Antonio Garrido Montalban, Sven M. Baum, Justin Cowell, Alexander McKillop,