Catalytic Asymmetric γ-Lactam Synthesis from Enolisable Anhydrides and Imines
An anion-binding approach to the problem of preparing enantioenriched γ-lactams from enolisable anhydrides and imines is reported. A simple bisurea catalyst promotes the cycloaddition between α-aryl succinic anhydrides and either PMP- or benzhydryl-protec
Collar, Aarón Gutiérrez,Trujillo, Cristina,Lockett-Walters, Bruce,Twamley, Brendan,Connon, Stephen J.
p. 7275 - 7279
(2019/05/15)
The base-catalysed Tamura cycloaddition reaction: Calculation, mechanism, isolation of intermediates and asymmetric catalysis
A combined experimental and computational investigation has revealed that the base-catalysed Tamura cycloaddition between homophthalic anhydride and activated alkenes/alkynes-a reaction previously thought of as a Diels-Alder type process-proceeds via a stepwise mechanism involving conjugate addition and ring closure; which allowed the first catalytic asymmetric α-substitution reactions to be demonstrated with up to >99% ee.
Lockett-Walters, Bruce,Trujillo, Cristina,Twamley, Brendan,Connon, Stephen
p. 11283 - 11286
(2019/09/30)
Catalytic, enantio- and diastereoselective synthesis of γ-butyrolactones incorporating quaternary stereocentres
A new, highly enantio- and diastereoselective catalytic asymmetric formal cycloaddition of aryl succinic anhydrides and aldehydes which generates paraconic acid (γ-butyrolactone) derivatives is reported.
Manoni, Francesco,Cornaggia, Claudio,Murray, James,Tallon, Sean,Connon, Stephen J.
p. 6502 - 6504
(2012/07/31)
Electrocarboxylation of alkynes with carbon dioxide in the presence of metal salt catalysts
With some common metal salts (CuI, FeCl3) as catalysts, alkynes can be effectively electrocarboxylated with CO2 (4 MPa) in an undivided cell with Ni cathode and Al sacrificial anode containing n-Bu4NBr-DMF as supporting el
Li, Chuanhua,Yuan, Gaoqing,Jiang, Huanfeng
experimental part
p. 1685 - 1689
(2011/07/07)
Synthesis of diverse lactam carboxamides leading to the discovery of a new transcription-factor inhibitor
(Chemical Equation Presented) Diversity is the key: Skeletal diversity is a useful starting point in the search for compounds that modulate protein-biopolymer interactions. A library of 400 lactam carboxamides has been synthesized in a short synthetic sequence and a new compound that inhibits the interaction of a transcription factor (HOXA13) with its DNA target has been discovered, and inhibition of transcription is demonstrated in cells.
Ng, Pui Yee,Tang, Yuchen,Knosp, Wendy M.,Stadler, H. Scott,Shaw, Jared T.
p. 5352 - 5355
(2008/03/27)
QUANTITATIVE DETERMINATION OF THE ELECTRONIC EFFECTS OF 3- AND 4-PYRIDAZINYL GROUPS FROM NMR SPECTRAL DATA FOR ISOMERIC AMINOPHENYL- AND PHENYLPYRIDAZINES
The previously unknown aminophenylpyridazines were synthesized.The inductive and resonance constants of 3- and 4-pyridazinyl groups were calculated on the basis of 1H and 13C NMR spectral data for isomeric aminophenyl- and phenylpyridazines in dimethyl sulfoxide (DMSO).
Shkurko, O. P.,Kuznetsov, S. A.,Denisov, A. Yu.,Mamaev, V. P.
p. 763 - 770
(2007/10/02)
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