One-Pot Synthesis of Symmetrical and Unsymmetrical Diketopiperazines from Unprotected Amino Acids

Anne Friedrich; Manuel Jainta; Martin Nieger; Stefan Bräse

doi:10.1055/s-2007-984875

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Synlett 2007(13): 2127-2129
DOI: 10.1055/s-2007-984875

LETTER

One-Pot Synthesis of Symmetrical and Unsymmetrical Diketopiperazines from Unprotected Amino Acids

Anne Friedrich^a, Manuel Jainta^a, Martin Nieger^b, Stefan Bräse*^a
^a Institute of Organic Chemistry, University of Karlsruhe (TH), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
Fax: +49(721)6088581; e-Mail: braese@ioc.uka.de;
^b Laboratory of Inorganic Chemistry, University of Helsinki, 00014 Helsinki, Finland

Further Information

Publication History

Received 25 April 2007
Publication Date:
27 June 2007 (online)

Abstract
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Abstract

An efficient synthesis of symmetrical and unsymmetrical proline-type diketopiperazines using a phosphite-promoted coupling was used to generate diketopiperazines with overall good yields from unprotected amino acids.

Key words

amino acids - diketopiperazines - thiolation - heterocycles

References and Notes

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CCDC-650358 contains the crystallographic data for 8a. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.uk/data_request/cif.