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Synthesis 2002(1): 0094-0098
DOI: 10.1055/s-2002-19295
DOI: 10.1055/s-2002-19295
PAPER
© Georg Thieme Verlag Stuttgart · New York
An Efficient Synthesis of (2S,6S)- and meso-Diaminopimelic Acids via Asymmetric Hydrogenation
Further Information
Received
5 June 2001
Publication Date:
04 August 2004 (online)
Publication History
Publication Date:
04 August 2004 (online)
Abstract
An efficient synthesis of the title compounds 1 and 2 has been successfully developed. The key step is the asymmetric hydrogenation of dehydroamino acid 7 using [Rh(I)(COD)-(S,S) or -(R,R)-Et-DuPHOS)]+OTf- to produce the optically active, protected amino acid derivatives in high ee (>95%). The approach also can be used for the synthesis of other isomers and analogues.
Key words
amino acids - diaminopimelic acids - asymmetric hydrogenation - DuPHOS - DAP analogues
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