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

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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