Silylcupration-mediated synthesis of 2-substituted allylamines

L Capella, A Degl'Innocenti, G Reginato…

Index: Capella, Laura; Degl'Innocenti, Alessandro; Reginato, Gianna; Ricci, Alfredo; Taddei, Maurizio; Seconi, Giancarlo Journal of Organic Chemistry, 1989 ,  vol. 54,  # 6  p. 1473 - 1476

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Citation Number: 37

Abstract

We report in this paper a new simple one-step procedure for the synthesis of a wide series of 1-silylallylic amines substituted at position 2 from the readily available3 precursor NJ-bis (trimethylsily1) propargylamine (1) by means of a silylcupration followed by in situ reaction with electrophiles, according to Scheme I. One of the most important aspects of the reaction in Scheme I turns out to be the inversion of regioselectivity in the addition of the reagents ...