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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
Autoren
Weitere Informationen
Publikationsverlauf
Received: 02. Dezember 2016
Accepted after revision: 09. Januar 2017
Publikationsdatum:
01. Februar 2017 (online)
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.
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