Synthesis of (3S,3S′,4S,4S′)-1,1′-ethylenedipyrrolidine-3,3′,4,4′-tetraol and related diamino diols: donor–acceptor hydrogen-bonding motifs of the C2 symmetric 3,4-dihydroxypyrrolidine unit |
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| Institution: | 1. Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon Street, London WC1H 0AJ, UK;2. Department of Chemistry, Queen Mary and Westfield College, University of London, London E1 4NS, UK;3. Department of Chemistry, The University of Southampton, Highfield, Southampton SO17 1BJ, UK;1. The Scientific Technological Center of Organic and Pharmaceutical Chemistry, Armenian Academy of Science, Institute of Fine Organic Chemistry of A.L.Mnjoyan, Yerevan 0014, Ave. Azatutyan 26, Armenia;2. Molecular Structure Research Center of the Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia, Yerevan 0014, Ave. Azatutyan 26, Armenia |
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| Abstract: | Enantiopure 1,1′-ethylenedipyrrolidines possessing 3,4-disubstitution have been prepared from esters of l-(+)-tartaric acid. Although diacylation routes via the diacetoxypyrrolidin-2,5-diones were problematic, N,N-dialkylation protocols proved to be reliable and led to the synthesis of (3S,3S′,4S,4S′)-1,1′-ethylenedipyrrolidine-3,3′,4,4′-tetraol, (3R,3′S,4R,4′S)-3,4-diamino-1,1′-ethylenedipyrrolidine-3′,4′-diol and (3R,3′R,4S,4′S)-3,3′-diamino-1,1′-ethylenedipyrrolidine-4,4′-diol. The tetraol possesses a crystal structure that exhibits an unusual zig-zag intermolecular pattern comprising a network of hydrogen bonds involving the terminal hydroxyl groups and a nitrogen atom of one of the pyrrolidine rings. |
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