34697-70-6Relevant articles and documents
Silicon Grignard Reagents as Nucleophiles in Transition-Metal-Catalyzed Allylic Substitution
Xue, Weichao,Oestreich, Martin
, p. 233 - 239 (2019/01/04)
A broad range of transition-metal catalysts is shown to promote allylic substitution reactions of allylic electrophiles with silicon Grignard reagents. The procedure was further elaborated for CuI as catalyst. The regioselectively is independent of the leaving group for primary allylic precursors, favoring α over γ. The stereochemical course of this allylic transposition was probed with a cyclic system, and anti -dia-stereoselectivity was obtained.
New findings on the regiochemistry of the silylcupration of allene
Blanco,Blanco, Francisco J.,Cuadrado,Cuadrado, Purificacion,Gonzalez,Gonzalez, Ana M.,Pulido,Pulido, Francisco J.,Fleming,Fleming, Ian
, p. 8881 - 8882 (2007/10/02)
Allene 1 reacts at -40*C with the phenyldimethylsilylcopper reagent 6, with the opposite regioselectivity to that shown by the corresponding silylcuprate reagent 2, to give allylsilanes 7 and 10-15 rather than vinylsilanes.
SILYL-CUPRATION OF ALLENE. A NEW ROUTE TO SILYLATED SYNTHONS
Cuadrado, P.,Gonzalez, A. M.,Pulido, F. J.
, p. 1825 - 1826 (2007/10/02)
Silyl-cupration of allene followed by treatment with iodine anomalously gives the vinyl iodide 4, a versatile synthetic intermediate.