Journal of Organic Chemistry p. 5243 - 5252 (1986)
Update date:2022-07-31
Topics:
Shea, Regan G.
Fitzner, Jeffrey N.
Fankhauser, John E.
Spaltenstein, Andreas
Carpino, Philip A.
et al.
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 <2,3>-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.
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