Header

UZH-Logo

Maintenance Infos

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.

Statistics

Citations

4 citations in Web of Science®
3 citations in Scopus®
Google Scholar™

Altmetrics

Downloads

26 downloads since deposited on 29 Apr 2015
14 downloads since 12 months
Detailed statistics

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:05 Apr 2016 19:14
Publisher:Elsevier
ISSN:0957-4166
Funders:National Science Center (Cracow) (Grant Preludium, UMO-2012/07/N/ST5/01873, Foundation of the University of Lodz
Publisher DOI:https://doi.org/10.1016/j.tetasy.2015.03.005

Download

Preview Icon on Download
Content: Published Version
Filetype: PDF - Registered users only
Size: 645kB
View at publisher
Preview Icon on Download
Preview
Content: Accepted Version
Filetype: PDF
Size: 163kB

TrendTerms

TrendTerms displays relevant terms of the abstract of this publication and related documents on a map. The terms and their relations were extracted from ZORA using word statistics. Their timelines are taken from ZORA as well. The bubble size of a term is proportional to the number of documents where the term occurs. Red, orange, yellow and green colors are used for terms that occur in the current document; red indicates high interlinkedness of a term with other terms, orange, yellow and green decreasing interlinkedness. Blue is used for terms that have a relation with the terms in this document, but occur in other documents.
You can navigate and zoom the map. Mouse-hovering a term displays its timeline, clicking it yields the associated documents.

Author Collaborations