38400-77-0Relevant academic research and scientific papers
Diastereoselective multicomponent cyclizations of fischer carbene complexes, lithium enolates, and allylmagnesium bromide leading to highly substituted five- and six-membered carbocycles
Barluenga, Jose,Perez-Sanchez, Ivan,Suero, Marcos G.,Rubio, Eduardo,Florez, Josefa
, p. 7225 - 7235 (2006)
The one-pot sequential reaction of a chromium alkoxycarbene complex, a ketone or ester lithium enolate, and allylmagnesium bromide enabled the selective synthesis of novel diastereomerically pure pentasubstituted cyclopentanols or tetrasubstituted 1,4-cyc
Indium(III) chloride-catalyzed coupling reaction of acid chlorides and allylic tins
Inoue,Shimizu,Shibata,Baba
, p. 1659 - 1661 (2001)
Allylic tributyltins and acid chlorides are effectively coupled to yield allylic ketones in indium(III) chloride-catalyzed reactions. In the case of γ-unsubstituted allylic tins, the assistance of a phosphine is essential to prevent further allylation of the produced ketones.
Ultrafast Grignard addition reactions in the presence of water
Osztrovszky, Gyorgyi,Holm, Torkil,Madsen, Robert
scheme or table, p. 3402 - 3404 (2010/08/21)
The addition of allylmagnesium bromide and benzylmagnesium chloride to carbonyl compounds was investigated in the presence of protic reagents such as water and the rate of carbonyl addition was found to be comparable to the rate of protonation by the reagent. The Royal Society of Chemistry 2010.
Solvent- and catalyst-free gem-bisallylation of carboxylic acid derivatives with allylzinc bromide
Wei, Yu-Juan,Ren, Heng,Wang, Jin-Xian
, p. 5697 - 5699 (2008/12/22)
A rapid and efficient procedure for the solvent-free synthesis of gem-bisallylation products has been achieved by allylzinc bromide with carboxylic acid derivatives in the absence of any catalysts at room temperature.
An efficient of Grignard-type procedure for the preparation of gem-diallylated compound
Shen, Kao-Hsien,Kuo, Chun-Wei,Yao, Ching-Fa
, p. 6348 - 6351 (2008/02/12)
An efficient and a new procedure for the conversion of various carboxylic acid derivatives into the corresponding gem-diallylated compound under mild reaction condition has been developed. The triallylaluminum mediated Grignard-type addition of carboxylic acid derivative was utilized as a key operation to affect the transformation. The procedure is operationally simple, giving good to excellent product yields for a broad range of substrates. The chemoselectivity and regioselectivity of triallylaluminum were also demonstrated.
Synthesis of β,γ-unsaturated ketones from acid chlorides through carbon-pentamethylcyclopentadienyl bond formation and cleavage
Uemura, Minoru,Iwasaki, Masayuki,Morita, Eiji,Yorimitsu, Hideki,Oshima, Koichiro
scheme or table, p. 2400 - 2405 (2009/09/26)
Reaction of acid chlorides with lithium pentamethylcyclopentadienide afforded the corresponding pentamethyl-cyclopentadienyl ketones in high yield. These ketones were treated with an allylaluminum reagent to form the corresponding 3-butenyl alcohols. Removal of pentamethylcyclopentadiene upon heating or treatment with a catalytic amount of trichloroacetic acid yielded the corresponding β,γ-unsaturated ketones in good yields.
Synthesis of β,γ-unsaturated ketones by allylation of pentamethylcyclopentadienyl ketones followed by removal of pentamethylcyclopentadiene
Iwasaki, Masayuki,Morita, Eiji,Uemura, Minoru,Yorimitsu, Hideki,Oshima, Koichiro
, p. 167 - 169 (2008/03/13)
A new route to β,γ-unsaturated ketones is disclosed. Aryl pentamethylcyclopentadienyl ketones underwent allylation with allyldimethylaluminum to yield the corresponding alcohols. Heating the alcohols in boiling toluene resulted in removal of pentamethylcy
A rapid and convenient synthesis of homoallylic alcohols by the barbier-grignard reaction
Sormunen, Grant J.,Lewis, David E.
, p. 3473 - 3480 (2007/10/03)
The use of the Barbier-Grignard reaction, where premixed allyl bromide and the carbonyl compound are added to magnesium in ether, is reported for the synthesis of homoallylic alcohols. This reaction provides good to excellent yields of most homoallylic alcohols with minimal formation of Wurtz coupling products.
Development of the traceless phenylhydrazide linker for solid-phase synthesis
Stieber, Frank,Grether, Uwe,Waldmann, Herbert
, p. 3270 - 3281 (2007/10/03)
The hydrazide group is a new oxidatively cleavable traceless linker for solid-phase chemistry. It can be readily introduced by hydrazide formation between a carboxy-functionalized resin and different substituted hydrazines. In order to achieve high yields in this step, new carboxylic acid resins were developed that are not prone to undesired imide formation upon activation of the carboxylic acid. The polymer-bound acyl hydrazides were successfully employed in various transformations, namely Heck, Suzuki, Sonogashira, and Stille couplings, as well as Wittig and Grignard reactions. Traceless release of the coupling products from the solid support is achieved selectively under mild conditions and in high purity by oxidation of the aryl hydrazides to acyl diazenes with CuII salts or N-bromosuccinimide (NBS) and subsequent nucleophilic attack of the acyl diazene intermediates. Traceless cleavage by oxidation with NBS can be carried out as a two-step process in which stable acyl diazenes are first generated by treatment with NBS in the absence of a nucleophile. After removal of the reagents by simple resin washing, the traceless release is effected by the addition of methanol, which leads to products of high purity without any additional separation steps.
Gem-diallylation of acyl azides with allylsamarium bromide under mild conditions
Li, Jian,Liu, Yongjun,Zhang, Yongmin
, p. 438 - 439 (2007/10/03)
Allylsamarium bromide reacts with acyl azides to give the corresponding gem-diallylation products, 4-alkyl-1,6-heptadienes-4-ols (3), in good to excellent yields. This novel reaction proceeds readily within a few minutes at room temperature.
