Now showing items 1-10 of 37
All-cis 1,2,3,4,5,6-hexafluorocyclohexane is a facially polarised cyclohexane
(2015-04) - Journal article,
The highest-energy stereoisomer of 1,2,3,4,5,6-hexafluorocyclohexane, in which all of the fluorines are ‘up’, is prepared in a 12-step protocol. The molecule adopts a classic chair conformation with alternate C–F bonds ...
Asymmetric isothiourea-catalysed formal [3+2] cycloadditions of ammonium enolates with oxaziridines
(2015-07-13) - Journal article,
A highly enantioselective Lewis base-catalysed formal [3+2] cycloaddition of ammonium enolates and oxaziridines to give stereodefined oxazolidin-4-ones in high yield is described. Employing an enantioenriched oxaziridine ...
Fluorine containing amino acids : synthesis and peptide coupling of amino acids containing the all-cis tetrafluorocyclohexyl motif
(2015-05-28) - Journal article,
A synthesis of two (S)-phenylalanine derivatives is described which have the all-cis, 2,3,5,6-tetrafluorocyclohexyl motif attached to the aromatic ring at the meta and para positions; the para substituted isomer is elaborated ...
Assessing dimerisation degree and cooperativity in a biomimetic small-molecule model by pulsed EPR
(2015-01) - Journal article,
Pulsed electron paramagnetic resonance (EPR) spectroscopy is gaining increasing importance as a complementary biophysical technique in structural biology. Here, we describe the synthesis, optimisation, and EPR titration ...
The use of residual dipolar coupling for conformational analysis of structurally related natural products
(2015-06) - Journal article,
Determining the conformational preferences of molecules in solution remains a considerable challenge. Recently, the use of residual dipolar coupling (RDC) analysis has emerged as a key method to address this. Whilst to ...
Synthesis of selectively fluorinated cyclohexanes : the observation of phenonium rearrangements during deoxyfluorination reactions on cyclohexane rings with a vicinal phenyl substituent
(2015) - Journal article,
A study focused on the synthesis of a derivative of all-cis phenyl-2,3,5,6-tetrafluorocyclohexane, incorporating a methyl group at the benzylic position, found that the fluorination reactions of diepoxide and diol precursors, ...
An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles : generality, applications and mechanistic investigations
(2015-02-14) - Journal article,
The reaction of L-serine derived N-arylnitrones with alkylarylketenes generates asymmetric 3-alkyl-3-aryloxindoles in good to excellent yields (up to 93%) and excellent enantioselectivity (up to 98% ee) via a pericyclic ...
Exploring the scope of the isothiourea-mediated synthesis of dihydropyridinones
(2015-02-21) - Journal article,
The exploration and expansion of the scope of the isothiourea-mediated synthesis of dihydropyridinones is presented. The use of ketimines derived from α,β-unsaturated γ-ketoesters as the Michael acceptor in a Michael ...
Stereo- and chemodivergent NHC-promoted functionalisation of arylalkylketenes with chloral
(2015-11-09) - Journal article,
Stereo- and chemodivergent enantioselective reaction pathways are observed upon treatment of alkylarylketenes and trichloroacetaldehyde (chloral) with N-heterocyclic carbenes, giving selectively either β-lactones (up to ...
Diphosphane 2,2′-binaphtho[1,8-de][1,3,2]dithiaphosphinine and the easy formation of a stable phosphorus radical cation
(2016-04-21) - Journal article,
A convenient synthesis route to 2,2’-binaphtho[1,8-de][1,3,2]di-thiaphosphinine (3) was found. Its stable radical cation 3•+ was accessed easily through one-electron oxidation with NOBF4.