94292-14-5Relevant academic research and scientific papers
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
Allylic Selenides in Organic Synthesis: New Methods for the Synthesis of Allylic Amines
Shea, Regan G.,Fitzner, Jeffrey N.,Fankhauser, John E.,Spaltenstein, Andreas,Carpino, Philip A.,et al.
, p. 5243 - 5252 (2007/10/02)
Oxidative rearrangement of allylic selenides in the presence of various amine nucleophiles provides synthetic access to a variety of allylic amine derivatives.The stereochemical outcome of these reactions has been investigated, and is consistent with a -sigmatropic rearrangement mechanism.Several D-α-amino acids and racemic β,γ-unsaturated α-amino acids were prepared in this manner.A variant of this process employing an achiral allylic selenide and chiral amide afforded protected allylic amines in low diastereoisomeric excess.
Asymmetric Carbon to Nitrogen Bond Formation Using Optically Active Allylic Selenides: A New General Method for the Synthesis of N-Protected Optically Active α-Amino Acids
Fitzner, Jeffrey N.,Shea, Regan G.,Fankhauser, John E.,Hopkins, Paul B.
, p. 417 - 419 (2007/10/02)
Optically active allylic selenides undergo oxidative sigmatropic rearrangement to afford optically active, protected allylic amines.The synthetic utility of this process is demonstrated by the synthesis of several N-protected D-α-amino acids in 78-84percent enantiomeric excess.
