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Synthesis 2002(1): 0063-0066
DOI: 10.1055/s-2002-19301
DOI: 10.1055/s-2002-19301
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Arylglycines by Reaction of Diethyl N-Boc-iminomalonate with Organomagnesium Reagents
Weitere Informationen
Received
26 July 2001
Publikationsdatum:
04. August 2004 (online)
Publikationsverlauf
Publikationsdatum:
04. August 2004 (online)
Abstract
Diethyl N-Boc-iminomalonate (3), prepared on multi-gram scale, served as a stable and highly reactive electrophilic glycine equivalent which reacted with organomagnesium compounds affording substituted aryl N-Boc-aminomalonates. Subsequent hydrolysis produced arylglycines.
Key words
amino acids - arylaminomalonates - arylglycines - imino esters - Grignard reactions
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References
As described in the experimental section, the best results were obtained by using 1.1 equivalents of iminomalonate 3 to drive the Grignard reaction to completion. However, the use of larger excess resulted in troublesome purification.