957765-75-2Relevant academic research and scientific papers
Use of Standard Addition to Quantify in Situ FTIR Reaction Data
Hutchinson, George,Welsh, Calum D. M.,Burés, Jordi
supporting information, p. 2012 - 2016 (2021/01/14)
FTIR spectroscopy is a common in situ reaction monitoring technique used in modern academic and industrial environments. The FTIR signals collected during the course of a reaction are proportional to the concentration of the reaction components but not intrinsically quantitative. To make FTIR data quantitative, precalibration or offline analyses of reaction samples are required, which diminishes the unique benefits of in situ reaction monitoring techniques. Herein, we report the use of standard addition as a convenient method to obtain quantitative FTIR data.
Rationalization of an unusual solvent-induced inversion of enantiomeric excess in organocatalytic selenylation of aldehydes
Bures, Jordi,Dingwall, Paul,Armstrong, Alan,Blackmond, Donna G.
supporting information, p. 8700 - 8704 (2014/08/18)
An unusual solvent-induced inversion of the sense of enantioselectivity observed in the α-selenylation of aldehydes catalyzed by a diphenylprolinol silyl ether catalyst is correlated to the presence of intermediates formed subsequent to the highly selective C-Se bond-forming step in the catalytic cycle. This work provides support for a mechanistic concept for enamine catalysis and includes a general role for "downstream intermediates" in selectivity outcomes in organocatalysis.
[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.
Enantioselective synthesis of α-alkyl,α-vinyl amino acids via [2,3]-sigmatropic rearrangement of selenimides
Armstrong, Alan,Emmerson, Daniel P. G.
supporting information; experimental part, p. 1040 - 1043 (2011/05/05)
Chiral α-alkyl,α-vinyl amino acids (quaternary vinyl glycine derivatives) are prepared with high levels of enantiomeric purity by [2,3]-sigmatropic rearrangement of allylic selenimides. The required trisubstituted allylic selenides are prepared by an orga
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
