Asymmetric Synthesis of Fused Polycyclic Indazoles through Aminocatalyzed Aza-Michael Addition/Intramolecular Cyclization

Autor:	Christine Greck, Maxime Giardinetti, Jerome Marrot, Vincent Coeffard, Xavier Moreau
Rok vydání:	2016
Předmět:	Indazole 010405 organic chemistry Stereochemistry Organic Chemistry Intramolecular cyclization Enantioselective synthesis Iminium 010402 general chemistry 01 natural sciences 0104 chemical sciences Enamine chemistry.chemical_compound chemistry Michael reaction
Zdroj:	The Journal of Organic Chemistry. 81:6855-6861
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.6b01201
Popis:	The first example of an asymmetric aminocatalyzed aza-Michael addition of 1H-indazole derivatives to α,β-unsaturated aldehydes is described. The iminium/enamine cascade process lies at the heart of our strategy, leading to enantioenriched fused polycyclic indazole architectures. Variations on both the α,β-unsaturated aldehydes and the indazole-7-carbaldehyde heterocycles were studied in order to broaden the scope of the transformation in synthetically interesting directions. The fused polycyclic indazoles exhibit fluorescence properties and can undergo synthetic transformations.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::acf868e0eb43291d71d9b21854985e51 https://doi.org/10.1021/acs.joc.6b01201 Zobrazit plný text záznamu