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Issue 17, 2014
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Diastereoselective Ireland–Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins

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Abstract

The diastereoselective Ireland–Claisen rearrangement of a range of substituted allyl β-amino esters gave the corresponding enantiopure α-substituted-β-amino esters with good diastereoselectivity. The application of this methodology in the asymmetric synthesis of a range of C(5)-substituted 1,2-anti-1,5-syn-transpentacins was demonstrated by the rearrangement of a range of β-amino esters derived from sorbic acid, followed by esterification, ring-closing metathesis, hydrogenolytic deprotection/reduction, and hydrolysis, which gave the C(5)-substituted transpentacins in only 9 steps from commercially available starting materials.

Graphical abstract: Diastereoselective Ireland–Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins

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Publication details

The article was received on 06 Feb 2014, accepted on 11 Mar 2014 and first published on 11 Mar 2014


Article type: Paper
DOI: 10.1039/C4OB00274A
Citation: Org. Biomol. Chem., 2014,12, 2702-2728
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    Diastereoselective Ireland–Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins

    S. G. Davies, A. M. Fletcher, J. A. Lee, P. M. Roberts, M. Y. Souleymanou, J. E. Thomson and C. M. Zammit, Org. Biomol. Chem., 2014, 12, 2702
    DOI: 10.1039/C4OB00274A

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