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Investigation of Diketopiperazines Containing a Guanidino‐Functionalized Sidechain as Potential Catalysts of Enantioselective Strecker Reactions
Author(s) -
Becker Christian,
Hoben Christine,
Schollmeyer Dieter,
Scherr Günther,
Kunz Horst
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500044
Subject(s) - chemistry , strecker amino acid synthesis , diketopiperazines , enantioselective synthesis , catalysis , phenylalanine , organic chemistry , stereochemistry , amino acid , biochemistry
Diketopiperazine 1 consisting of L ‐(γ‐guanidino‐α‐amino)butyric acid and L ‐phenylalanine was synthesized as the hydroacetate and as the hydronitrate. Its structure was confirmed by X‐ray analysis. In contrast to reports in the literature (Lipton et al.), compound 1 does not induce enantioselevtive catalysis of Strecker reactions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)