Co-reporter:Mark E. Wood, Sabine Bissiriou, Christopher Lowe and Kim M. Windeatt
Organic & Biomolecular Chemistry 2013 vol. 11(Issue 16) pp:2712-2723
Publication Date(Web):05 Mar 2013
DOI:10.1039/C3OB40275D
Using C-3 di-deuterated morpholin-2-ones bearing N-2-iodobenzyl and N-3-bromobut-3-enyl radical generating groups, only products derived from the more stabilised C-3, rather than the less stabilised C-5 translocated radicals, were formed after intramolecular 1,5-hydrogen atom transfer, suggesting that any kinetic isotope effect present was not sufficient to offset captodative stabilisation.
Co-reporter:Mark E. Wood, Sabine Bissiriou, Christopher Lowe, Andrew M. Norrish, Katell Sénéchal, Kim M. Windeatt, Simon J. Coles and Michael B. Hursthouse
Organic & Biomolecular Chemistry 2010 vol. 8(Issue 20) pp:4653-4665
Publication Date(Web):17 Aug 2010
DOI:10.1039/C0OB00205D
The extent to which deuterium can act as a protecting group to prevent unwanted 1,5-hydrogen atom transfer to aryl and vinyl radical intermediates was examined in the context of the generation of α-aminoalkyl radicals in a pyrrolidine ring. Intra- and intermolecular radical trapping following hydrogen atom transfer provides an illustration of the use of the primary kinetic isotope effect in directing the outcome of synthetic C–C bond-forming processes.
Co-reporter:Muhammad I. Chowdhry, Peter N. Horton, Michael B. Hursthouse, Mark E. Wood
Tetrahedron Letters 2009 50(26) pp: 3400-3403
Publication Date(Web):
DOI:10.1016/j.tetlet.2009.02.110
Co-reporter:Mark E. Wood, Sabine Bissiriou, Christopher Lowe and Kim M. Windeatt
Organic & Biomolecular Chemistry 2008 vol. 6(Issue 17) pp:3048-3051
Publication Date(Web):22 Jul 2008
DOI:10.1039/B810018G
Competition experiments have been carried out to determine the extent to which deuterium can be used as a protecting group for carbon–hydrogen bonds in radical-based intramolecular hydrogen atom transfer processes.
Co-reporter:Mark E. Wood, Victoria M. Annis and Clifford D. Jones
Organic & Biomolecular Chemistry 2008 vol. 6(Issue 22) pp:4099-4101
Publication Date(Web):01 Oct 2008
DOI:10.1039/B814677B
Crystalline samples of three N-aroyl-1,2,4-dithiazolidine-3,5-diones have been prepared as the first examples of a novel class of compound that displays the reactivity of an acyl isocyanate when treated with nucleophiles.
Co-reporter:Mark E. Wood, Mark J. Penny, Jenny S. Steere, Peter N. Horton, Mark E. Light and Michael B. Hursthouse
Chemical Communications 2006 (Issue 28) pp:2983-2985
Publication Date(Web):07 Jun 2006
DOI:10.1039/B604123J
A radical-based approach facilitates the highly stereocontrolled functionalisation of β-amino alcohols, opening up a new, generally applicable methodology for the preparation of quaternary α-amino acids.
Co-reporter:Mark E. Wood, Daniel J. Cane-Honeysett, Michael D. Dowle, Simon J. Coles and Michael B. Hursthouse
Organic & Biomolecular Chemistry 2003 vol. 1(Issue 17) pp:3015-3023
Publication Date(Web):29 Jul 2003
DOI:10.1039/B305096C
Methods have been developed for the N-alkylation of 1,2,4-dithiazolidine-3,5-dione 2 and the subsequent conversion of the N-alkylated derivatives into isocyanates 5. An extension of this methodology onto a solid-support is also reported. X-ray crystallographic analysis has been carried out on potassium 1,2,4-dithiazolidine-3,5-dione 3 for structural comparison with the parent heterocycle 2.
Co-reporter:Mark E. Wood, Daniel J. Cane-Honeysett and Michael D. Dowle
Organic & Biomolecular Chemistry 2002 (Issue 18) pp:2046-2047
Publication Date(Web):19 Aug 2002
DOI:10.1039/B206793E
1,2,4-Dithiazolidine-3,5-dione 1 can be used as a nitrogen nucleophile in a modified Mitsunobu procedure to give N-alkylated products 2 which can be converted via isocyanates, into amine derivatives, under very mild conditions.
Co-reporter:Norio Shibata, Jack E. Baldwin, Mark E. Wood
Bioorganic & Medicinal Chemistry Letters 1997 Volume 7(Issue 4) pp:413-416
Publication Date(Web):18 February 1997
DOI:10.1016/S0960-894X(97)00023-1
A library of 7240 TentaGel® resin-bound peptides all containing the active site residues of isopenicillin N synthase was prepared. Several peptides showed a high binding affinity for Co2+.A library of 7240 TentaGelR̊ resin-bound peptides all containing the active site residues of isopenicillin N synthase was prepared, Several peptides showed a high binding affinity for Co2+.
Co-reporter:Mark E. Wood, Victoria M. Annis and Clifford D. Jones
Organic & Biomolecular Chemistry 2008 - vol. 6(Issue 22) pp:NaN4101-4101
Publication Date(Web):2008/10/01
DOI:10.1039/B814677B
Crystalline samples of three N-aroyl-1,2,4-dithiazolidine-3,5-diones have been prepared as the first examples of a novel class of compound that displays the reactivity of an acyl isocyanate when treated with nucleophiles.
Co-reporter:Mark E. Wood, Sabine Bissiriou, Christopher Lowe and Kim M. Windeatt
Organic & Biomolecular Chemistry 2008 - vol. 6(Issue 17) pp:NaN3051-3051
Publication Date(Web):2008/07/22
DOI:10.1039/B810018G
Competition experiments have been carried out to determine the extent to which deuterium can be used as a protecting group for carbon–hydrogen bonds in radical-based intramolecular hydrogen atom transfer processes.
Co-reporter:Mark E. Wood, Sabine Bissiriou, Christopher Lowe, Andrew M. Norrish, Katell Sénéchal, Kim M. Windeatt, Simon J. Coles and Michael B. Hursthouse
Organic & Biomolecular Chemistry 2010 - vol. 8(Issue 20) pp:NaN4665-4665
Publication Date(Web):2010/08/17
DOI:10.1039/C0OB00205D
The extent to which deuterium can act as a protecting group to prevent unwanted 1,5-hydrogen atom transfer to aryl and vinyl radical intermediates was examined in the context of the generation of α-aminoalkyl radicals in a pyrrolidine ring. Intra- and intermolecular radical trapping following hydrogen atom transfer provides an illustration of the use of the primary kinetic isotope effect in directing the outcome of synthetic C–C bond-forming processes.
Co-reporter:Mark E. Wood, Sabine Bissiriou, Christopher Lowe and Kim M. Windeatt
Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 16) pp:NaN2723-2723
Publication Date(Web):2013/03/05
DOI:10.1039/C3OB40275D
Using C-3 di-deuterated morpholin-2-ones bearing N-2-iodobenzyl and N-3-bromobut-3-enyl radical generating groups, only products derived from the more stabilised C-3, rather than the less stabilised C-5 translocated radicals, were formed after intramolecular 1,5-hydrogen atom transfer, suggesting that any kinetic isotope effect present was not sufficient to offset captodative stabilisation.