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Synlett 2004(15): 2791-2793
DOI: 10.1055/s-2004-835639
DOI: 10.1055/s-2004-835639
LETTER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Chiral α-Amino-diazoketones on Solid Support: An Access to β-Homologated Amino Acid Derivatives
Weitere Informationen
Received
31 August 2004
Publikationsdatum:
08. November 2004 (online)
Publikationsverlauf
Publikationsdatum:
08. November 2004 (online)
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Abstract
Diazoketone derivatives were obtained on solid support from their corresponding α-amino acids anchored by their N-terminus to the resin. A complete study was performed to optimize the two steps process of this synthesis on solid support: activation of the carboxylic acid function followed by reaction with diazomethane. The obtained diazoketones were then submitted to Wolff rearrangement in the presence of an amine to yield the corresponding homologated amides or in the presence of water to yield the corresponding β-homologated amino acids.
Key words
α-amino-diazoketone - Wolff rearrangement - solid-phase synthesis - inverse anchoring
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