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Enantioselective NHC-catalysed redox [4+2]-hetero-Diels-Alder reactions using α-aroyloxyaldehydes and unsaturated ketoesters

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Enantioselective NHC-catalysed redox [4+2]-hetero-Diels-Alder reactions using α-aroyloxyaldehydes and unsaturated ketoesters. / Taylor, James E.; Davies, Alyn T.; Douglas, James J.; Churchill, Gwydion; Smith, Andrew D.

In: Tetrahedron: Asymmetry, Vol. 28, No. 2, 15.02.2017, p. 355-366.

Research output: Contribution to journalArticlepeer-review

Harvard

Taylor, JE, Davies, AT, Douglas, JJ, Churchill, G & Smith, AD 2017, 'Enantioselective NHC-catalysed redox [4+2]-hetero-Diels-Alder reactions using α-aroyloxyaldehydes and unsaturated ketoesters', Tetrahedron: Asymmetry, vol. 28, no. 2, pp. 355-366. https://doi.org/10.1016/j.tetasy.2017.01.002

APA

Taylor, J. E., Davies, A. T., Douglas, J. J., Churchill, G., & Smith, A. D. (2017). Enantioselective NHC-catalysed redox [4+2]-hetero-Diels-Alder reactions using α-aroyloxyaldehydes and unsaturated ketoesters. Tetrahedron: Asymmetry, 28(2), 355-366. https://doi.org/10.1016/j.tetasy.2017.01.002

Vancouver

Taylor JE, Davies AT, Douglas JJ, Churchill G, Smith AD. Enantioselective NHC-catalysed redox [4+2]-hetero-Diels-Alder reactions using α-aroyloxyaldehydes and unsaturated ketoesters. Tetrahedron: Asymmetry. 2017 Feb 15;28(2):355-366. https://doi.org/10.1016/j.tetasy.2017.01.002

Author

Taylor, James E. ; Davies, Alyn T. ; Douglas, James J. ; Churchill, Gwydion ; Smith, Andrew D. / Enantioselective NHC-catalysed redox [4+2]-hetero-Diels-Alder reactions using α-aroyloxyaldehydes and unsaturated ketoesters. In: Tetrahedron: Asymmetry. 2017 ; Vol. 28, No. 2. pp. 355-366.

Bibtex - Download

@article{b2d93aadb6c048f7abe549f5adacc7ee,
title = "Enantioselective NHC-catalysed redox [4+2]-hetero-Diels-Alder reactions using α-aroyloxyaldehydes and unsaturated ketoesters",
abstract = "N-Heterocyclic carbene (NHC)-catalysed redox [4+2]-hetero-Diels-Alder reactions of α-aroyloxyaldehydes with either β,γ-unsaturated α-ketoesters or α,β-unsaturated γ-ketoesters generates substituted syn-dihydropyranones in good yield with excellent enantioselectivity (up to >99:1 er). The product diastereoselectivity is markedly dependent upon the nature of the unsaturated enone substituent. The presence of either electron-neutral or electron-rich aryl substituents gives excellent diastereoselectivity (up to >99:5 dr), while electron-deficient aryl substituents give reduced diastereoselectivity. In these cases, the syn-dihydropyranone products are more susceptible to base-promoted epimerisation at the C(4)-position under the reaction conditions, accounting for the lower diastereoselectivity obtained.",
author = "Taylor, {James E.} and Davies, {Alyn T.} and Douglas, {James J.} and Gwydion Churchill and Smith, {Andrew D.}",
note = "The authors thank the European Research Council under the European Union{\textquoteright}s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850 (J.E.T. and A.T.D.) as well as the EPSRC, UK and AstraZeneca plc, UK (Case award to J.J.D.) for financial support. A.D.S. thanks the Royal Society, London, UK, for a Wolfson Merit Award. ",
year = "2017",
month = feb,
day = "15",
doi = "10.1016/j.tetasy.2017.01.002",
language = "English",
volume = "28",
pages = "355--366",
journal = "Tetrahedron: Asymmetry",
issn = "0957-4166",
publisher = "Elsevier",
number = "2",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Enantioselective NHC-catalysed redox [4+2]-hetero-Diels-Alder reactions using α-aroyloxyaldehydes and unsaturated ketoesters

AU - Taylor, James E.

AU - Davies, Alyn T.

AU - Douglas, James J.

AU - Churchill, Gwydion

AU - Smith, Andrew D.

N1 - The authors thank the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850 (J.E.T. and A.T.D.) as well as the EPSRC, UK and AstraZeneca plc, UK (Case award to J.J.D.) for financial support. A.D.S. thanks the Royal Society, London, UK, for a Wolfson Merit Award.

PY - 2017/2/15

Y1 - 2017/2/15

N2 - N-Heterocyclic carbene (NHC)-catalysed redox [4+2]-hetero-Diels-Alder reactions of α-aroyloxyaldehydes with either β,γ-unsaturated α-ketoesters or α,β-unsaturated γ-ketoesters generates substituted syn-dihydropyranones in good yield with excellent enantioselectivity (up to >99:1 er). The product diastereoselectivity is markedly dependent upon the nature of the unsaturated enone substituent. The presence of either electron-neutral or electron-rich aryl substituents gives excellent diastereoselectivity (up to >99:5 dr), while electron-deficient aryl substituents give reduced diastereoselectivity. In these cases, the syn-dihydropyranone products are more susceptible to base-promoted epimerisation at the C(4)-position under the reaction conditions, accounting for the lower diastereoselectivity obtained.

AB - N-Heterocyclic carbene (NHC)-catalysed redox [4+2]-hetero-Diels-Alder reactions of α-aroyloxyaldehydes with either β,γ-unsaturated α-ketoesters or α,β-unsaturated γ-ketoesters generates substituted syn-dihydropyranones in good yield with excellent enantioselectivity (up to >99:1 er). The product diastereoselectivity is markedly dependent upon the nature of the unsaturated enone substituent. The presence of either electron-neutral or electron-rich aryl substituents gives excellent diastereoselectivity (up to >99:5 dr), while electron-deficient aryl substituents give reduced diastereoselectivity. In these cases, the syn-dihydropyranone products are more susceptible to base-promoted epimerisation at the C(4)-position under the reaction conditions, accounting for the lower diastereoselectivity obtained.

UR - http://www.sciencedirect.com/science/article/pii/S095741661630475X#appd002

U2 - 10.1016/j.tetasy.2017.01.002

DO - 10.1016/j.tetasy.2017.01.002

M3 - Article

VL - 28

SP - 355

EP - 366

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

SN - 0957-4166

IS - 2

ER -

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