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Synthesis 2017; 49(09): 2003-2008
DOI: 10.1055/s-0036-1588694
DOI: 10.1055/s-0036-1588694
paper
Chiral Building Blocks Based on 1,2-Disubstituted Diamantanes
Further Information
Publication History
Received: 02 December 2016
Accepted after revision: 09 January 2017
Publication Date:
01 February 2017 (online)
![](https://www.thieme-connect.de/media/synthesis/201709/lookinside/thumbnails/ss-2016-t0829-op_10-1055_s-0036-1588694-1.jpg)
Abstract
The reaction of 1-hydroxydiamantane with elemental bromine leads to consecutive cage opening and re-closure, thereby providing a straightforward approach to the class of previously unknown 1,2-disubstituted diamondoid derivatives. Functional group exchange gave, among others, chiral bidentate ligands 1,2-dihydroxy- and 1,2-diaminodiamantane. The latter was enantioseparated on gram scale with ee >98% through a single crystallization with (+)-tartaric acid.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588694.
- Supporting Information
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