Preparation of α-substituted γ-alkoxyallylstannanes from β-tributylstannyl acrolein acetals: scope of the method and primary rationalization of the obtained results

F Fliegel, I Beaudet, S Watrelot-Bourdeau…

Index: Fliegel, Florian; Beaudet, Isabelle; Watrelot-Bourdeau, Sandrine; Cornet, Nicolas; Quintard, Jean-Paul Journal of Organometallic Chemistry, 2005 , vol. 690, # 3 p. 659 - 673

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Citation Number: 2

Abstract

α-Substituted γ-alkoxyallylstannanes were obtained from β-tributylstannyl acrolein acetals when reacted with lower order magnesium cyanocuprates in the presence of boron trifluoride at low temperature. In the case of n-alkylcyanocuprates an anti SN2′ substitution on a cisoid conformation appears to be the main reaction pathway. However, subtle competitions with other mechanisms may occur depending on the experimental conditions ...