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

Louis C. Morrill; Daniel G. Stark; James E. Taylor; Siobhan R. Smith; James A. Squires; Agathe C.A. D'Hollander; Carmen Simal; Peter Shapland; Timothy J.C. O'Riordan; Andrew 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

Louis C. Morrill, Daniel G. Stark, James E. Taylor, Siobhan R. Smith, James A. Squires, Agathe C.A. D'Hollander, Carmen Simal, Peter Shapland, Timothy J.C. O'Riordan, Andrew D. Smith

Department of Chemistry

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

37 Citations (SciVal)

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 CCl₃ 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. This journal is

Original language	English
Pages (from-to)	9016-9027
Number of pages	12
Journal	Organic and 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

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Morrill, L. C., Stark, D. G., Taylor, J. E., Smith, S. R., Squires, J. A., D'Hollander, A. C. A., Simal, 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 and Biomolecular Chemistry, 12(44), 9016-9027. https://doi.org/10.1039/c4ob01788a

Morrill, LC, Stark, DG, Taylor, JE, Smith, SR, Squires, JA, D'Hollander, ACA, Simal, 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 and Biomolecular Chemistry, vol. 12, no. 44, pp. 9016-9027. https://doi.org/10.1039/c4ob01788a

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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 CCl3 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. This journal is",

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AU - Smith, Siobhan R.

AU - Squires, James A.

AU - D'Hollander, Agathe C.A.

AU - Simal, Carmen

AU - Shapland, Peter

AU - O'Riordan, Timothy J.C.

AU - Smith, Andrew D.

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

Abstract

ASJC Scopus subject areas

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