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Synlett 2014; 25(07): 1026-1030
DOI: 10.1055/s-0033-1340859
DOI: 10.1055/s-0033-1340859
letter
Facile Preparation of 1,5-Diazacyclooctanes from Unsaturated Imines: Effects of the Hydroxyl Groups on [4+4] Dimerization
Further Information
Publication History
Received: 08 January 2014
Accepted after revision: 04 February 2014
Publication Date:
18 March 2014 (online)
![](https://www.thieme-connect.de/media/synlett/201407/lookinside/thumbnails/10.1055-s-0033-1340859-1.jpg)
Abstract
Hydroxyl groups on an unsaturated imine, which may be readily obtained from the corresponding unsaturated aldehyde and the 1,2-ethanolamine derivative, were found to efficiently activate a [4+4] dimerization reaction to produce the eight-membered 1,5-diazacyclooctane. A novel OH–π interaction between the two imines, in addition to the stabilization of the eight-membered diacetals, was proposed based on density functional theory calculations.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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Reference
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