Skip to content

Research at St Andrews

Enantioselective synthesis of β-fluoro-β-aryl-α-amino pentenamides by organocatalytic [2,3]-sigmatropic rearrangement

Research output: Contribution to journalArticle

DOI

Abstract

The tetramisole-promoted catalytic enantioselective [2,3]-sigmatropic rearrangement of quaternary ammonium salts bearing a (Z)-3-fluoro-3-arylprop-2-ene group generates, after addition of benzylamine, a range of β-fluoro-β-aryl-α-aminopentenamides containing a stereogenic tertiary fluorine substituent. Cyclic and acyclic nitrogen substituents as well as various aromatic substituents are tolerated, giving the β-fluoro-β-aryl-α-aminopentenamide products in up to 76% yield, 96:4 dr, and 98:2 er.
Close

Details

Original languageEnglish
Pages (from-to)5182-5185
Number of pages4
JournalOrganic Letters
Volume19
Issue number19
Early online date8 Sep 2017
DOIs
StatePublished - 6 Oct 2017

    Research areas

  • Flluorinated amino-acids, Allylic ammonium ylides, Kinetic resolution, Medicinal chemistry, Protein design, Catalysts, Mannich, Benzotetramisole, Straightforward, Cycloaddition

Discover related content
Find related publications, people, projects and more using interactive charts.

View graph of relations

Related by author

  1. Isothiourea-catalyzed enantioselective addition of 4-nitrophenyl esters to iminium ions

    Arokianathar, J. N., Frost, A. B., Slawin, A. M. Z., Stead, D. & Smith, A. D. 12 Dec 2017 In : ACS Catalysis. In press

    Research output: Contribution to journalArticle

  2. Aryloxide-facilitated catalyst turnover in enantioselective α,β-unsaturated acyl ammonium catalysis

    Matviitsuk, A., Greenhalgh, M., Barrios Antunez, D., Slawin, A. & Smith, A. D. 25 Aug 2017 In : Angewandte Chemie International Edition. Early View

    Research output: Contribution to journalArticle

  3. 6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis

    N P, R. M., Cordes, D. B., Slawin, A. M. Z. & Smith, A. D. 28 Feb 2017 In : Chemical Communications. 53, 17, p. 2555-2558

    Research output: Contribution to journalArticle

Related by journal

  1. Diastereoselective and branched-aldehyde-selective tandem hydroformylation-hemiaminal formation: synthesis of functionalized piperidines and amino-alcohols

    Pittaway, R., Fuentes, J. A. & Clarke, M. L. 2 Jun 2017 In : Organic Letters. 19, 11, p. 2845-2848 4 p.

    Research output: Contribution to journalArticle

  2. Organocatalytic Synthesis of Fused Bicyclic 2,3-Dihydro-1,3,4-oxadiazoles through an Intramolecular Cascade Cyclization

    Fugard, A. J., Thompson, B. K., Slawin, A. M. Z., Taylor, J. E. & Smith, A. D. 4 Dec 2015 In : Organic Letters. 17, 23, p. 5824-5827 4 p.

    Research output: Contribution to journalArticle

  3. Total synthesis and biological evaluation of the tetramic acid based natural product harzianic acid and its stereoisomers

    Healy, A. R., Vinale, F., Lorito, M. & Westwood, N. J. 6 Feb 2015 In : Organic Letters. 17, 3, p. 692-695 4 p.

    Research output: Contribution to journalArticle

  4. Synthesis of di-, tri-, and tetrasubstituted pyridines from (phenylthio)carboxylic acids and 2-[aryl(tosylimino)methyl]acrylates

    Stark, D. G., O’Riordan, T. J. C. & Smith, A. D. 8 Dec 2014 In : Organic Letters. In press

    Research output: Contribution to journalArticle

ID: 250962719