Allylic selenides in organic synthesis: New methods for the synthesis of allylic amines

RG Shea, JN Fitzner, JE Fankhauser…

Index: Shea, Regan G.; Fitzner, Jeffrey N.; Fankhauser, John E.; Spaltenstein, Andreas; Carpino, Philip A.; et al. Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5243 - 5252

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Citation Number: 74

Abstract

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 Da-aminO acids and racemic &y-unsaturated a-amino acids were prepared in this manner. A variant of this process employing an achiral allylic ...