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Synthesis of diastereomerically pure 1,4,5-substituted-2-oxopiperazines on solid-phase

✍ Scribed by Nawaz M Khan; Montserrat Cano; Shankar Balasubramanian

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 190 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)00268-x

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✦ Synopsis

The first studies toward the solid-phase synthesis of 1,4,5-substituted-2-oxopiperazines are reported. The synthetic strategy is based on reductive alkylation of resin-bound amino acids using N-protected a-amino aldehydes (with concomitant epimerization), followed by acylation with a-chloroacetyl chloride. Subsequent stereoselective on-bead intramolecular cyclization has led to a diastereomerically pure 2-oxopiperazine.

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