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 C-2 symmetric 3,4-dihydroxypyrrolidine unit

Marson, Charles M., Melling, Robert C., Coles, Simon J. and Hursthouse, Michael B. (2005) 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 C-2 symmetric 3,4-dihydroxypyrrolidine unit. Tetrahedron: Asymmetry, 16 (16), 2799-2809. (doi:10.1016/j.tetasy.2005.07.024).

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'-tetraoi, (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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Contributors

Author: Simon J. Coles

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