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Synthesis 2014; 46(06): 787-798
DOI: 10.1055/s-0033-1338583
paper
© Georg Thieme Verlag Stuttgart · New York

Efficient Preparation of Apically Substituted Diamondoid Derivatives

Paul Kahl
a   Institute of Organic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 58, 35392 Giessen, Germany   Fax: +49(641)9934309   Email: prs@uni-giessen.de
,
Boryslav A. Tkachenko
a   Institute of Organic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 58, 35392 Giessen, Germany   Fax: +49(641)9934309   Email: prs@uni-giessen.de
,
Anatoliy A. Novikovsky
b   Department of Organic Chemistry, Kiev Polytechnic Institute, pr. Pobedy 37, 03056 Kiev, Ukraine    Email: aaf@xtf.ntu-kpi.kiev.ua
,
Jonathan Becker
c   Institute of Inorganic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 58, 35392 Giessen, Germany
,
Jeremy E. P. Dahl
d   Stanford University, Stanford Institute for Materials & Energy Science, 476 Lomita Mall, Stanford, CA 94305, USA
,
Robert M. K. Carlson
d   Stanford University, Stanford Institute for Materials & Energy Science, 476 Lomita Mall, Stanford, CA 94305, USA
,
Andrey A. Fokin*
a   Institute of Organic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 58, 35392 Giessen, Germany   Fax: +49(641)9934309   Email: prs@uni-giessen.de
b   Department of Organic Chemistry, Kiev Polytechnic Institute, pr. Pobedy 37, 03056 Kiev, Ukraine    Email: aaf@xtf.ntu-kpi.kiev.ua
,
Peter R. Schreiner*
a   Institute of Organic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 58, 35392 Giessen, Germany   Fax: +49(641)9934309   Email: prs@uni-giessen.de
› Author Affiliations
Further Information

Publication History

Received: 30 November 2013

Accepted: 13 December 2013

Publication Date:
10 January 2014 (online)

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Abstract

We present an effective three-step chromatography-free sequence for the preparation of apical monohydroxy derivatives of diamantane, triamantane, and [121]tetramantane from the corresponding bis-apical diols utilizing tert-butyldimethylsilyl chloride as the monosilylating agent. The procedure was successfully applied to the monoprotection of several other aliphatic and aromatic diols. Additionally, 9-aminodiamantan-4-carboxylic acid, which has significant potential in medicinal and material sciences, was prepared through Ritter reaction of 4,9-dihydroxydiamantane in trifluoroacetic acid.

Key words

amino acids - diols - monoprotection - nanostructures - silyl protecting groups

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
  • Supporting Information
 

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