144723-87-5Relevant academic research and scientific papers
Gallium-mediated allyl transfer from bulky homoallylic alcohol to aldehydes via retro-allylation: Stereoselective synthesis of both erythro- and threo-homoallylic alcohols
Hayashi, Sayuri,Hirano, Koji,Yorimitsu, Hideki,Oshima, Koichiro
, p. 3577 - 3579 (2005)
(Chemical Equation Presented) Retro-allylation of bulky gallium homoallylic alkoxides occurs to generate (Z)- and (E)-crotylgallium reagents stereospecifically, starting from erythro- and threo-homoallylic alcohols, respectively. The (Z)- and (E)-crotylgallium reagents immediately reacted with aromatic aldehydes to afford the corresponding erythro and threo-homoallylic alcohols, respectively.
[bmim][Br] as an Inexpensive and Efficient Medium for the Barbier-Type Allylation Reaction Using a Catalytic Amount of Indium: Mechanistic Studies
Dey, Papiya,Koli, Mrunesh,Goswami, Dibakar,Sharma, Anubha,Chattopadhyay, Subrata
, p. 1333 - 1341 (2018/04/02)
Barbier-type allylation reactions of aldehydes and ketones have been carried out with both unsubstituted and γ-substituted allyl bromides using only a catalytic amount (0.1 equiv.) of In metal in [bmim][Br], but not in H2O, organic solvents, or
Gallium-mediated allyl transfer from bulky homoallyl alcohol to aldehydes or alkynes: Control of dynamic σ-allylgalliums based on retro-allylation reaction
Hayashi, Sayuri,Hirano, Koji,Yorimitsu, Hideki,Oshima, Koichiro
, p. 505 - 513 (2008/02/06)
A new method for the preparation and control of dynamic σ-allylgalliums is disclosed. Upon treatment with a Grignard reagent and gallium trichloride, bulky homoallyl alcohols undergo gallium-mediated retro-allylation reaction to provide σ-allylgallium reagents. The σ-allylgallium reagents generated were applied to carbonyl allylation. The retro-allylation reaction generates (Z)- and (E)-σ-crotylgalliums stereospecifically, starting from erythro- and threo-homoallyl alcohols, respectively. The stereochemically defined crotylgallium reagents effected stereoselective allylation of aldehydes. Allylgallation reaction of alkynes with the allylgallium reagents prepared by retro-allylation is also described.
The employment of indium nanoparticles in Barbier-type reaction of allylic chloride in water
Li, Jiaming,Zha, Zhenggen,Sun, Lilin,Zhang, Yan,Wang, Zhiyong
, p. 498 - 499 (2007/10/03)
Indium nanoparticles have been employed in the reactions of various carbonyl compounds with allyl (crotyl) chloride in water, affording the corresponding alcohols with high yields. The crotylation gave exclusive γ-adducts with a dominant syn-isomer. Copyr
