Organocatalytic Michael addition–lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents

L.C. Morrill; D.G. Stark; J.E. Taylor; S.R. Smith; J.A. Squires; A.C.A. D'Hollander; Carmen Simal Fernandez; P. Shapland; T.J.C. O'Riordan; A.D. Smith

doi:10.1039/c4ob01788a

Organocatalytic Michael addition–lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents

L.C. Morrill, D.G. Stark, J.E. Taylor, S.R. Smith, J.A. Squires, A.C.A. D'Hollander, Carmen Simal Fernandez, P. Shapland, T.J.C. O'Riordan, A.D. Smith

Research output: Contribution to journal › Article › peer-review

34 Citations (Scopus)

Abstract

Isothiourea HBTM-2.1 catalyses the Michael addition-lactonisation of 2-aryl and 2-alkenylacetic acids and α,β-unsaturated trichloromethyl ketones. Ring-opening of the resulting dihydropyranones and subsequent alcoholysis of the CCl ketone with an excess of methanol gives a range of diesters in high diastereo- and enantioselectivity (up to 95:5 dr and >99% ee). Sequential addition of two different nucleophiles to a dihydropyranone gives the corresponding differentially substituted diacid derivative.

Original language	English
Pages (from-to)	9016-9027
Number of pages	12
Journal	Organic & Biomolecular Chemistry
Volume	12
Issue number	44
Early online date	6 Oct 2014
DOIs	https://doi.org/10.1039/c4ob01788a
Publication status	Published - 28 Nov 2014

Access to Document

10.1039/c4ob01788a

Smith_2014_OBC_Organocatalytic_AM
© Royal Society of Chemistry 2014. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at http://dx.doi.org/10.1039/C4OB01788A
Accepted author manuscript, 1.06 MB

Cite this

Morrill, L. C., Stark, D. G., Taylor, J. E., Smith, S. R., Squires, J. A., D'Hollander, A. C. A., Simal Fernandez, C., Shapland, P., O'Riordan, T. J. C., & Smith, A. D. (2014). Organocatalytic Michael addition–lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents. Organic & Biomolecular Chemistry, 12(44), 9016-9027. https://doi.org/10.1039/c4ob01788a

@article{1cf02a60efac4ccaad87b571a49c017f,

title = "Organocatalytic Michael addition–lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents",

abstract = "Isothiourea HBTM-2.1 catalyses the Michael addition-lactonisation of 2-aryl and 2-alkenylacetic acids and α,β-unsaturated trichloromethyl ketones. Ring-opening of the resulting dihydropyranones and subsequent alcoholysis of the CCl ketone with an excess of methanol gives a range of diesters in high diastereo- and enantioselectivity (up to 95:5 dr and >99% ee). Sequential addition of two different nucleophiles to a dihydropyranone gives the corresponding differentially substituted diacid derivative.",

author = "L.C. Morrill and D.G. Stark and J.E. Taylor and S.R. Smith and J.A. Squires and A.C.A. D'Hollander and {Simal Fernandez}, Carmen and P. Shapland and T.J.C. O'Riordan and A.D. Smith",

note = "The authors thank the Royal Society for a University Research Fellowship (ADS), The Carnegie Trust for the Universities of Scotland (LCM), Syngenta/EPSRC (Case award to DGS), GSK/EPSRC (CASE award to SRS), the EU (IEF for CS), and the European Research Council under the European Union's Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement no. 279850 (JET) for funding. ",

year = "2014",

month = nov,

day = "28",

doi = "10.1039/c4ob01788a",

language = "English",

volume = "12",

pages = "9016--9027",

journal = "Organic & Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "44",

}

Morrill, LC, Stark, DG, Taylor, JE, Smith, SR, Squires, JA, D'Hollander, ACA, Simal Fernandez, C, Shapland, P, O'Riordan, TJC & Smith, AD 2014, 'Organocatalytic Michael addition–lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents', Organic & Biomolecular Chemistry, vol. 12, no. 44, pp. 9016-9027. https://doi.org/10.1039/c4ob01788a

TY - JOUR

T1 - Organocatalytic Michael addition–lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents

AU - Morrill, L.C.

AU - Stark, D.G.

AU - Taylor, J.E.

AU - Smith, S.R.

AU - Squires, J.A.

AU - D'Hollander, A.C.A.

AU - Simal Fernandez, Carmen

AU - Shapland, P.

AU - O'Riordan, T.J.C.

AU - Smith, A.D.

N1 - The authors thank the Royal Society for a University Research Fellowship (ADS), The Carnegie Trust for the Universities of Scotland (LCM), Syngenta/EPSRC (Case award to DGS), GSK/EPSRC (CASE award to SRS), the EU (IEF for CS), and the European Research Council under the European Union's Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement no. 279850 (JET) for funding.

PY - 2014/11/28

Y1 - 2014/11/28

N2 - Isothiourea HBTM-2.1 catalyses the Michael addition-lactonisation of 2-aryl and 2-alkenylacetic acids and α,β-unsaturated trichloromethyl ketones. Ring-opening of the resulting dihydropyranones and subsequent alcoholysis of the CCl ketone with an excess of methanol gives a range of diesters in high diastereo- and enantioselectivity (up to 95:5 dr and >99% ee). Sequential addition of two different nucleophiles to a dihydropyranone gives the corresponding differentially substituted diacid derivative.

AB - Isothiourea HBTM-2.1 catalyses the Michael addition-lactonisation of 2-aryl and 2-alkenylacetic acids and α,β-unsaturated trichloromethyl ketones. Ring-opening of the resulting dihydropyranones and subsequent alcoholysis of the CCl ketone with an excess of methanol gives a range of diesters in high diastereo- and enantioselectivity (up to 95:5 dr and >99% ee). Sequential addition of two different nucleophiles to a dihydropyranone gives the corresponding differentially substituted diacid derivative.

U2 - 10.1039/c4ob01788a

DO - 10.1039/c4ob01788a

M3 - Article

AN - SCOPUS:84908377573

SN - 1477-0520

VL - 12

SP - 9016

EP - 9027

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 44

ER -

Organocatalytic Michael addition–lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents

Abstract

Access to Document

Fingerprint

Cite this