Formation of N-substituted 4- and 7-oxo-4,5,6,7-tetrahydroindoles revisited: a mechanistic interpretation and conversion into 4- and 7-oxoindoles

Autor:	Sven M. Baum, Justin K. Cowell, Alexander McKillop, A. G. Montalban
Rok vydání:	2012
Předmět:	Stereospecificity Chemistry Computational chemistry Impurity Stereochemistry Organic Chemistry Drug Discovery Aromatization Chirality (chemistry) Biochemistry Interpretation (model theory)
Zdroj:	Tetrahedron Letters. 53:4276-4279
ISSN:	0040-4039
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::a0081a2b11b7cc6d51e84260fdf994ac https://doi.org/10.1016/j.tetlet.2012.05.090 Zobrazit plný text záznamu Full Text from ScienceDirect