68260-37-7Relevant academic research and scientific papers
Silicon Grignard Reagents as Nucleophiles in Transition-Metal-Catalyzed Allylic Substitution
Xue, Weichao,Oestreich, Martin
, p. 233 - 239 (2019)
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.
Practical synthesis of allylic silanes from allylic esters and carbamates by stereoselective copper-catalyzed allylic substitution reactions
Oestreich, Martin,Auer, Gertrud
, p. 637 - 640 (2007/10/03)
The first copper-catalyzed allylic substitution reactions of allylic acetates and carbamates employing a bis(triorganosilyl)zinc reagent are reported. This novel procedure avoids the use of stoichiometric amounts of copper salts which are usually mandatory with this chemistry. Application of this methodology to standard model substrates substantiates a high diastereoselectivity for the double bond geometry (E:Z) as well as the relative configuration (syn:anti).
Regioselective 1,4-silylcupration of 1,3-dienes - Characterization and electrophilic trapping of the intermediate σ-allyl)copper complex
Liepins, Vilnis,Baeckvall, Jan-E.
, p. 3527 - 3535 (2007/10/03)
Silylcupration reactions of 1,3-dienes with a cyanocuprate reagent PhMe2SiCuCNLi produce a (4-silyl-2-alken-1-yl)-copper complex, which was trapped by electrophiles. The use of allylic phosphates as electrophiles resulted in highly regioselecti
Silylcupration of 1,3-dienes followed by an electrophilic trapping reaction
Liepins, Vilnis,Baeckvall, Jan-E
, p. 1861 - 1864 (2007/10/03)
(matrix presented) Silylcupration reaction of 1,3-dienes with a cyanocuprate reagent, PhMe2SiCuCNLi, followed by an electrophilic trapping has been reported for the first time. The use of allylic phosphates as electrophiles resulted in a highly
Reaction of triorgano(triorganogermyl)silanes with alkaly-metal allyl alcoholates
Kabaki,Inoue,Sato
, p. 459 - 466 (2007/10/02)
Reaction of the lithium alcoholates of 1-vinylcyclohexanol (2a) (±)-linalool (2b), and 1-octen-3-ol (2c) with (dimethylphenylgermyl)trimethylsilane (3a) gave selective the corresponding allyldimethylphenylgermane derivatives (5a,c,e). Similar treatment with dimethylphenyl(trimethylgermyl)silane (3b) gave mixtures of the allyltrimethylgermanes (5b,d,f) and allyldimethylphenylsilanes (7b,d,f), whereas use of the potassium alcoholates afforded selectively 5b,d,f.
