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Synthesis 2006(18): 3092-3098
DOI: 10.1055/s-2006-950181
DOI: 10.1055/s-2006-950181
PAPER
© Georg Thieme Verlag Stuttgart · New York
A New Approach to the Synthesis of β-Amino Acids
Further Information
Received
23 March 2006
Publication Date:
15 August 2006 (online)
Publication History
Publication Date:
15 August 2006 (online)
Abstract
A detailed study of the addition of the dianions of carboxylic acids to isocyanates is presented. The use of sub-stoichiometric amounts of the amine in the generation of the dianion leads to an optimized process, which prevents the formation of urea derivatives due to the secondary reaction of isocyanates with the amine. This methodology is a new approach to the synthesis of β-amino acids with better control of α-substitution than previously described.
Key words
amino acids - catalysis - isocyanates - regioselectivity - dianions
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