94202-83-2Relevant academic research and scientific papers
First principles design of derivatizing agent for direct determination of enantiomeric purity of chiral alcohols and amines by NMR spectroscopy
Orlov, Nikolay V.,Ananikov, Valentine P.
scheme or table, p. 3212 - 3214 (2010/09/04)
77Se NMR offers superior sensing of chirality within the structure of the diastereomers (Δδ up to 6.1 ppm), compared to 13C (Δδ 1H (Δδ 0.2 ppm). The developed procedure is equally well suitable for determina
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.
