- Synthesis of Protected Racemic β,γ-Unsaturated-α-Amino Acids via γ-Phenylseleno-α,β-Unsaturated Esters
Oxidative rearrangement of γ-phenylseleno-α,β-unsaturated esters (1) with the N-chlorosuccinimide/N,N-diisopropylethylamine/alkyl carbamate reagent combination affords preparatively useful yields of protected β,γ-unsaturated-α-amino acids (2).
- Fitzner, Jeffrey N.,Pratt, Daniel V.,Hopkins, Paul B.
p. 1959 - 1962
(2007/10/02)
- Allylic Selenides in Organic Synthesis: New Methods for the Synthesis of Allylic Amines
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.
- Shea, Regan G.,Fitzner, Jeffrey N.,Fankhauser, John E.,Spaltenstein, Andreas,Carpino, Philip A.,et al.
p. 5243 - 5252
(2007/10/02)