Synthesis 2017; 49(09): 2003-2008
DOI: 10.1055/s-0036-1588694
paper
© Georg Thieme Verlag Stuttgart · New York

Chiral Building Blocks Based on 1,2-Disubstituted Diamantanes

Andrey A. Fokin*
a   Department of Organic Chemistry, Kiev Polytechnic Institute, Pr. Pobedy 37, 03056 Kiev, Ukraine   Email: aaf@xtf.kpi.ua
b   Institute of Organic Chemistry, Justus-Liebig-Universität, Heinrich-Buff-Ring 17, 35392 Giessen, Germany   Email: prs@uni-giessen.de
,
Alexander E. Pashenko
a   Department of Organic Chemistry, Kiev Polytechnic Institute, Pr. Pobedy 37, 03056 Kiev, Ukraine   Email: aaf@xtf.kpi.ua
,
Vladyslav V. Bakhonsky
a   Department of Organic Chemistry, Kiev Polytechnic Institute, Pr. Pobedy 37, 03056 Kiev, Ukraine   Email: aaf@xtf.kpi.ua
b   Institute of Organic Chemistry, Justus-Liebig-Universität, Heinrich-Buff-Ring 17, 35392 Giessen, Germany   Email: prs@uni-giessen.de
,
Tatyana S. Zhuk
a   Department of Organic Chemistry, Kiev Polytechnic Institute, Pr. Pobedy 37, 03056 Kiev, Ukraine   Email: aaf@xtf.kpi.ua
,
Lesya V. Chernish
a   Department of Organic Chemistry, Kiev Polytechnic Institute, Pr. Pobedy 37, 03056 Kiev, Ukraine   Email: aaf@xtf.kpi.ua
,
Pavel A. Gunchenko
a   Department of Organic Chemistry, Kiev Polytechnic Institute, Pr. Pobedy 37, 03056 Kiev, Ukraine   Email: aaf@xtf.kpi.ua
b   Institute of Organic Chemistry, Justus-Liebig-Universität, Heinrich-Buff-Ring 17, 35392 Giessen, Germany   Email: prs@uni-giessen.de
,
Andrey O. Kushko
a   Department of Organic Chemistry, Kiev Polytechnic Institute, Pr. Pobedy 37, 03056 Kiev, Ukraine   Email: aaf@xtf.kpi.ua
,
Jonathan Becker
c   Institute of Inorganic and Analytical Chemistry, Justus-Liebig-Universität, Heinrich-Buff-Ring 17, 35392 Giessen, Germany
,
Raffael C. Wende
b   Institute of Organic Chemistry, Justus-Liebig-Universität, Heinrich-Buff-Ring 17, 35392 Giessen, Germany   Email: prs@uni-giessen.de
,
Peter R. Schreiner*
b   Institute of Organic Chemistry, Justus-Liebig-Universität, Heinrich-Buff-Ring 17, 35392 Giessen, Germany   Email: prs@uni-giessen.de
› Author Affiliations
Further Information

Publication History

Received: 02 December 2016

Accepted after revision: 09 January 2017

Publication Date:
01 February 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

 
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