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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

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
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
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.
direct optical resolution, molecular recognition, natural occurrence, chemistry, alcohols
0957-4166
2799-2809
Marson, Charles M.
28f9225a-51fa-4c2b-848c-b77b225f53cb
Melling, Robert C.
e454b0cc-4177-453e-be23-94c1e8587cb4
Coles, Simon J.
65bb28e4-4917-43f5-a770-a00017d6783f
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Marson, Charles M.
28f9225a-51fa-4c2b-848c-b77b225f53cb
Melling, Robert C.
e454b0cc-4177-453e-be23-94c1e8587cb4
Coles, Simon J.
65bb28e4-4917-43f5-a770-a00017d6783f
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28

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).

Record type: Article

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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More information

Published date: 22 August 2005
Keywords: direct optical resolution, molecular recognition, natural occurrence, chemistry, alcohols

Identifiers

Local EPrints ID: 20861
URI: http://eprints.soton.ac.uk/id/eprint/20861
ISSN: 0957-4166
PURE UUID: 526a53a5-99f5-4799-adbb-19bae1f12178

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Date deposited: 02 Mar 2006
Last modified: 06 Oct 2020 23:43

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