Facile synthesis of d-amino acids from an l-serine-derived aziridine

Using the concept that l-serine can be converted into a desymmetrized γ-diol derivative, five d-amino acids were synthesized from a common aziridine intermediate by a general, high-yielding three-step process. The key 2- t-butyldimethylsiloxymethyl N- t-butoxycarbonyl aziridine intermediate was synt...

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Bibliographic Details
Published in:Tetrahedron letters 1998-12, Vol.39 (51), p.9389-9392
Main Authors: Travins, Jeremy M., Etzkorn, Felicia A.
Format: Article
Language:English
Subjects:
amino acids and derivatives
asymmetry
aziridines
copper and compounds
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Summary:Using the concept that l-serine can be converted into a desymmetrized γ-diol derivative, five d-amino acids were synthesized from a common aziridine intermediate by a general, high-yielding three-step process. The key 2- t-butyldimethylsiloxymethyl N- t-butoxycarbonyl aziridine intermediate was synthesized in four steps and 65% overall yield. Using the concept that l-serine can be converted into a desymmetrized γ-diol, five d-amino acids were synthesized from a common aziridine intermediate.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)02198-4