Asymmetric Synthesis of a Protected Dihydroxypiperazic Acid Derivative

Abstract

A short and flexible route for the synthesis of 1,2-diisopropyl-3-methyl-(3S,4R,5R)-4,5-dihydroxyhexahydro-1,2,3-pyrid­azinetricarboxylate, from readily available acrolein, is described. This approach involves an asymmetric α-hydrazination, dihydroxylation and intramolecular cyclisation as key steps.

Key words

piperazic acid - l-proline - α-hydrazination - dihydroxylation - intramolecular cyclisation

References

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19

Enantiomeric excess was 88%, which was determined by HPLC (Shimadzu LC-10 AT pump) using a CHIRALCEL OB-H Diacel column (250 × 4.6 mm; hexane-i-PrOH-EtOH, 80:10:10; flow rate 1.0 mL/min) with UV detection at 254 nm (SPD-10A UV detector).