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Synthesis 1992; 1992(11): 1150-1156
DOI: 10.1055/s-1992-26324
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Ein einfacher Zugang zu Aminosäuren mit einer Diazofunktion in der Seitenkette ausgehend von Asparaginsäure

Klaus Burger* , Martin Rudolph, Horst Neuhauser, Manuel Gold
  • *Institut für Organische Chemie der Technischen Universität München, Lichtenbergstr. 4, D-8046 Garching, Germany
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Publication History

Publication Date:
17 September 2002 (online)

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A Simple Approach to Amino Acids with a Diazo Function in the Side Chain Starting from Aspartic Acid [2,2-Bis(trifluoromethyl)-5-oxo-1,3-oxazolidin-4-yl]acetic acid chloride (2) and diazoalkanes react to give the amino acid derivatives 2,2-bis(trifluoromethyl)-4-(3-diazo-2-oxopropyl)-1,3-oxazolidin-5-ones 3. Compounds 3 are useful intermediates for the synthesis of various natural and nonnatural α-amino acids and their derivatives. The synthetic potential is demonstrated i.a. by syntheses of 2-amino-5-hydroxy-4-oxopentanoic acid and 2-amino-4-oxohexanoic acid derivatives.

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