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Synthesis 2009(22): 3751-3756  
DOI: 10.1055/s-0029-1217024
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Synthesis of (R)- and (S)-α-(Hydroxymethyl)pyroglutamic Acid Esters from l-Proline

Tetsuro Shinada*, Hiroki Yoshida, Yasufumi Ohfune*
Graduate School of Science, Osaka City University, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan
Fax: +81(6)66053153; e-Mail: shinada@sci.osaka-cu.ac.jp; e-Mail: ohfune@sci.osaka-cu.ac.jp;
Further Information

Publication History

Received 2 June 2009
Publication Date:
23 September 2009 (online)

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Abstract

An efficient synthesis of (R)- and (S)-α-(hydroxymethyl)pyroglutamic acid esters from l-proline has been achieved. Each step was carried out on a decagram scale to access the N-protected (R)-ester in a highly efficient manner (44% overall yield from a proline-derived bicyclic substrate).

Key words

amino acids - α-substituted proline - pyroglutamic acid esters - stereoselective synthesis - alkylations

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