104937-86-2Relevant academic research and scientific papers
A NEW SYNTHESIS OF SECONDARY ALLYLIC ALIPHATIC AND AROMATIC AMINES.
Spaltenstein, Andreas,Carpino, Philip A.,Hopkins, Paul B.
, p. 147 - 150 (2007/10/02)
Treatment of a variety of aliphatic or aromatic primary amines with an N-chlorosuccinimide-activated allylic selenide affords in modest to good yield the corresponding allylically rearranged secondary amines.Examples are reported which define the scope an
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.
