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Synthesis 2004(18): 3065-3069  
DOI: 10.1055/s-2004-834918
PAPER
© Georg Thieme Verlag Stuttgart · New York

Hexafluoroacetone as Protecting and Activating Reagent: Site-Selective Functionalization of α-Amino Alkanedioic Acids

Thomas Rühl*a, Christoph Böttchera, Ksenia Pumpora, Lothar Henniga, Joachim Sielerb, Klaus Burger*a
a Department of Organic Chemistry, University of Leipzig, Johannisallee 29, 04103 Leipzig, Germany
Fax: +49(341)9736599; e-Mail: burger@organik.chemie.uni-leipzig.de;
b Department of Inorganic Chemistry, University of Leipzig, Linnéstraße 3, 04103 Leipzig, Germany
Further Information

Publication History

Received 7 July 2004
Publication Date:
08 November 2004 (online)

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Abstract

Methodology for the site-selective functionalization of α-amino alkanedioic acids (Asp, Glu and homologues) using hexa­fluoroacetone as protecting and activating reagent is described. Via new types of dielectrophiles, alternative approaches to multifunctional non-natural amino acids and some of their conjugates become readily available.

Key words

hexafluoroacetone - fluorine - DAST - diacylation - ω-carboxy-activation - amino acids

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19

Details on the structure are available on request from Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, UK on quoting depository number CCDC 235280.

26

Radics, G.; Spengler, J.; Koksch, B.; Berger, S.; Burger, K., manuscript in preparation.