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Davies SG, Fletcher AM, Lee JA, et al. Diastereoselective Ireland-Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins. Org Biomol Chem. 2014;12(17):2702-28doi: 10.1039/c4ob00274a.
Davies, S. G., Fletcher, A. M., Lee, J. A., Roberts, P. M., Souleymanou, M. Y., Thomson, J. E., & Zammit, C. M. (2014). Diastereoselective Ireland-Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins. Organic & biomolecular chemistry, 12(17), 2702-28. https://doi.org/10.1039/c4ob00274a
Davies, Stephen G, et al. "Diastereoselective Ireland-Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins." Organic & biomolecular chemistry vol. 12,17 (2014): 2702-28. doi: https://doi.org/10.1039/c4ob00274a
Davies SG, Fletcher AM, Lee JA, Roberts PM, Souleymanou MY, Thomson JE, Zammit CM. Diastereoselective Ireland-Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins. Org Biomol Chem. 2014 May 07;12(17):2702-28. doi: 10.1039/c4ob00274a. PMID: 24647746.
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Org Biomol Chem. 2014 May 07;12(17):2702-28. doi: 10.1039/c4ob00274a.

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

Organic & biomolecular chemistry

Stephen G Davies, Ai M Fletcher, James A Lee, Paul M Roberts, Myriam Y Souleymanou, James E Thomson, Charlotte M Zammit

Affiliations

  1. Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK. [email protected].

PMID: 24647746 DOI: 10.1039/c4ob00274a

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.

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