92622-33-8Relevant academic research and scientific papers
[2,3]-sigmatropic rearrangement of allylic selenimides: Strategy for the synthesis of peptides, peptidomimetics, and N-aryl vinyl glycines
Armstrong, Alan,Emmerson, Daniel P. G.,Milner, Harry J.,Sheppard, Robert J.
, p. 3895 - 3907 (2014/05/20)
The scope of the NCS-mediated amination/[2,3]-sigmatropic rearrangement of enantioenriched allylic selenides has been expanded to provide access to three new product classes. The use of N-protected amino acid amides provides a novel strategy for accessing peptide chains containing unnatural vinyl glycine amino acid residues. Also reported is the use of amino acid esters, allowing the diastereoselective synthesis of N,N-dicarboxymethylamines, a motif found in a number of pharmaceuticals. Furthermore, use of a range of N-aromatic and N-heteroaromatic amines allows the formation of enantioenriched N-arylamino acids, a motif found in a number of synthetically and biologically interesting compounds.
Polystyrene-supported organocatalysts for α-selenenylation and Michael reactions: A common post-modification approach for catalytic differentiation
Giacalone, Francesco,Gruttadauria, Michelangelo,Agrigento, Paola,Campisciano, Vincenzo,Noto, Renato
experimental part, p. 75 - 80 (2012/02/03)
Three different resin-supported catalysts have been prepared by using the well established post-modification approach by means of thiol-ene coupling reaction. Two catalysts were tested for the first time in the asymmetric α-selenenylation of propanal, whi
Organocatalytic asymmetric α-selenenylation of aldehydes
Tiecco, Marcello,Carlone, Armando,Sternativo, Silvia,Marini, Francesca,Bartoli, Giuseppe,Melchiorre, Paolo
, p. 6882 - 6885 (2008/09/18)
(Figure Presented) Getting round the (periodic) table: The enamine activation concept has been extended to the asymmetric addition of selenium-based compounds to aldehydes in an organocatalytic transformation that provides high reaction efficiency and ste
Stereoselective total syntheses of the naturally occurring enantiomers of N-acetylneuraminic acid and 3-deoxy-D-manno-2-octulosonic acid. A new and stereospecific approach to sialo and 3-deoxy-D-manno-2-octulosonic acid conjugates
Danishefsky,DeNinno,Chen
, p. 3929 - 3940 (2007/10/02)
The total syntheses of the title compounds have been achieved. A critical element of these syntheses was the concept of using a furan ring as a surrogate for a carboxylic acid. The furyl diene 22 reacted with the R and S enantiomers of 2-(phenylseleno)pro
Total Synthesis of (+/-)-3-Deoxy-D-manno-2-octulopyranosonate (KDO)
Danishefsky, Samuel J.,Pearson, William H.,Segmuller, Brigitte E.
, p. 1280 - 1285 (2007/10/02)
Cyclocondensation of 2-(phenylseleno)propionaldehyde with 1-(α-furyl)-1-methoxy-3--4-(benzoyloxy)-1,3-butadiene under the influence of boron trifluoride produces a predominance (2.4:1) of cis-/trans-3-(benzoyloxy)-6-(α-furyl)-2-(1-ph
