Stereochemistry of piperazine-2,5-dione formation by self-condensation of DL-amino acid esters

Hiroshi Naraoka, Kaoru Harada

研究成果: ジャーナルへの寄稿学術誌査読

6 被引用数 (Scopus)

抄録

'Racemic' piperazine-2,5-diones (diketopiperazines, dkps) have been synthesized by the self-condensation of DL-amino acid esters without solvent. It was found that 'racemic' dkps consisted of cis-and trans-isomers, and that cis-dkp was preferentially formed in the early stage of the self-condensation, the cis:trans ratios gradually decreasing with increasing reaction time. These results may be attributed to the difference in the rates of cyclization of two kinds of diastereoisomeric dipeptide esters, intermediates in the formation of dkps from DL-amino acid esters. It was further confirmed that the pre-cis-dipeptide ester, which formed cis-dkp, cyclized faster than the pre-trans-dipeptide ester in methanol. Differences in steric hindrance in the cyclization reaction of pre-cis- and pre-trans-isomers may be an important factor in the stereochemistry of self-condensation.

本文言語英語
ページ(範囲)1557-1560
ページ数4
ジャーナルJournal of the Chemical Society, Perkin Transactions 1
DOI
出版ステータス出版済み - 1986
外部発表はい

!!!All Science Journal Classification (ASJC) codes

  • 化学 (全般)

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