Enantiomerically Enriched Bicyclic Hydroxamic Acids in One Step from α-Aminohydroxamic Acids and Keto Acids via Cyclocondensation

New enantiomerically enriched bicyclic hydroxamic acids, 1-hydroxy-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones, have been synthesized by the cyclocondensation of L- α -aminohydroxamic acids with keto acids in a highly chemo- and stereoselective manner. The cis configuration between the amin...

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Published inSynthetic communications Vol. 43; no. 18; pp. 2484 - 2492
Main Authors Hoshino, Yujiro, Oyaizu, Masanori, Koyanagi, Yoko, Honda, Kiyoshi
Format Journal Article
LanguageEnglish
Published Taylor & Francis Group 17.09.2013
Subjects
Chiral compounds
cyclocondensation
hydroxamic acids
keto acids
N-hydroxyimidazolidinones
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Summary:New enantiomerically enriched bicyclic hydroxamic acids, 1-hydroxy-dihydro-1H-pyrrolo[1,2-a]imidazole-2,5(3H,6H)-diones, have been synthesized by the cyclocondensation of L- α -aminohydroxamic acids with keto acids in a highly chemo- and stereoselective manner. The cis configuration between the amino acid side chain and the methyl group at C7a in 1H-pyrrolo[1,2-a]imidazole-2,5-dione was unambiguously established by X-ray crystallographic analysis. This method could also be applied to the cyclocondensation with o-formylbenzoic acid, giving a tricyclic hydroxamic acid in a good yield. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2012.717162