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Synthesis of optically active polycyclic N-heterocycles derived from L-prolinamine


Wroblewska, Aneta; Mloston, Grzegorz; Heimgartner, Heinz (2015). Synthesis of optically active polycyclic N-heterocycles derived from L-prolinamine. Tetrahedron: Asymmetry, 26(8/9):505-509.

Abstract

The N-Boc-protected (S)-prolinamine reacts readily with formaldehyde and diverse alpha-hydroxyimino ketones to give imidazole N-oxides with an enantiomerically pure N-protected (pyrrolidin-2-yl)methyl substituent. Subsequent deprotection yields the corresponding NH derivatives. Upon treatment of these products with Ac2O at room temperature, a cascade of reactions leads to optically active tricyclic products. In all these processes, the stereogenic center is preserved. In one case, the bis-heterocyclic imidazole N-oxide was transformed into the corresponding optically active imidazole-2-thione via a sulfur-transfer reaction with 2,2,4,4-tetramethylcyclobutane-1,3-dithione.

Abstract

The N-Boc-protected (S)-prolinamine reacts readily with formaldehyde and diverse alpha-hydroxyimino ketones to give imidazole N-oxides with an enantiomerically pure N-protected (pyrrolidin-2-yl)methyl substituent. Subsequent deprotection yields the corresponding NH derivatives. Upon treatment of these products with Ac2O at room temperature, a cascade of reactions leads to optically active tricyclic products. In all these processes, the stereogenic center is preserved. In one case, the bis-heterocyclic imidazole N-oxide was transformed into the corresponding optically active imidazole-2-thione via a sulfur-transfer reaction with 2,2,4,4-tetramethylcyclobutane-1,3-dithione.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:April 2015
Deposited On:29 Apr 2015 15:29
Last Modified:18 Apr 2018 11:46
Publisher:Elsevier
ISSN:0957-4166
Funders:National Science Center (Cracow) (Grant Preludium, UMO-2012/07/N/ST5/01873, Foundation of the University of Lodz
OA Status:Green
Publisher DOI:https://doi.org/10.1016/j.tetasy.2015.03.005

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