Publication detail

New synthetic pathway leading to 2-nitroindan-1-ols using intramolecular Henry reaction

Authors: Hanusek Jiří | Valtr Jakub | Dostálová Kamila

Year: 2016

Type of publication: ostatní - přednáška nebo poster

Page from-to: nestránkováno

Titles:

Language	Name	Abstract	Keywords
eng	New synthetic pathway leading to 2-nitroindan-1-ols using intramolecular Henry reaction	We suggested and carried out original multistep synthesis of several 2-nitroethylbenzaldehydes and cyclize them to corresponding 2-nitroindan-1-ols. First we studied kinetics of cyclization step in tertiary amine buffers. We found that the reaction is subject to general-base catalysis i.e. the formation of reactive carbanion is rate-limiting step of the cyclization. Moreover for parent 2-nitroethylbenzaldehyde (R = H) triple-phase kinetics was observed. Next we studied the diastereoselectivity of the cyclization reaction. Moderate diastereoselectivity (d.r. ca 5:1) was observed for both starting aldehydes with R = H and CH3 when TEA was used as a base. This diastereoselectivity dramatically changed (d.r. 1:2.5) for derivative with R = H when much weaker Cu(OAc)2·L (L = optically pure stereoisomer of 5-tert-butyl-2,5-dimethyl-2-(pyridin-2-yl)imidazolidin-4-one) catalyst was used for cyclization.

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