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Issue 63, 2013
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Asymmetric syntheses of enantiopure C(5)-substituted transpentacins via diastereoselective Ireland–Claisen rearrangements

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Abstract

Asymmetric syntheses of (S,S,S)-2-amino-5-methylcyclopentanecarboxylic acid and (S,S,S)-2-amino-5-phenylcyclopentanecarboxylic acid were achieved in 9 steps from commercially available starting materials via the Ireland–Claisen rearrangement of two enantiopure β-amino allyl esters, followed by ring-closing metathesis, reduction and deprotection.

Graphical abstract: Asymmetric syntheses of enantiopure C(5)-substituted transpentacins via diastereoselective Ireland–Claisen rearrangements

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Publication details

The article was received on 02 May 2013, accepted on 26 Jun 2013 and first published on 27 Jun 2013


Article type: Communication
DOI: 10.1039/C3CC43250E
Citation: Chem. Commun., 2013,49, 7037-7039
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    Asymmetric syntheses of enantiopure C(5)-substituted transpentacins via diastereoselective Ireland–Claisen rearrangements

    S. G. Davies, A. M. Fletcher, P. M. Roberts, J. E. Thomson and C. M. Zammit, Chem. Commun., 2013, 49, 7037
    DOI: 10.1039/C3CC43250E

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