119619-39-5Relevant articles and documents
Mild and efficient barbier allylation reaction mediated by magnesium powder under solvent-free conditions
Li, Shunxi,Wang, Jin-Xian,Wen, Xiaoliu,Ma, Xiaofang
, p. 849 - 855 (2011)
A novel and highly efficient synthesis of homoallylic alcohols is achieved by the allylation of carbonyl compounds using magnesium powder as mediator under solvent-free conditions. A series of aldehydes and ketones are converted to the corresponding homoa
Chemoselective allylation of aldehydes using cerium(III) chloride: Simple synthesis of homoallylic alcohols
Yadav,Reddy,Kondaji,Shyam Sunder Reddy
, p. 879 - 882 (2005)
Aldehydes undergo smooth nucleophilic addition with allyltributylstannane in the presence of CeCl3·7H2O in acetonitrile under extremely mild reaction conditions to afford the corresponding homoallylic alcohols in excellent yields wit
Wittig rearrangement of allyl and propargyl furfuryl ethers leading to 2-furylmethanol derivatives
Tsubuki, Masayoshi,Kamata, Teruyoshi,Okita, Hiroyuki,Arai, Mayumi,Shigihara, Atsushi,Honda, Toshio
, p. 2263 - 2264 (1999)
The first example of the Wittig rearrangement of furfuryl ethers is presented and its application to the preparation of 3-(2-furyl)-3-hydroxy-2- methylpropionates is described.
Synthesis and biological evaluation of optically active conjugated γ- And δ-lactone derivatives
Ardan, Melis,Sezer, Serdar,Guenel, Aslihan,Akkaya, Mahinur,Tanyeli, Cihangir
, p. 5814 - 5818,5 (2012)
An efficient synthesis of racemic and both enantiomeric forms of heteroaryl substituted γ- and δ-lactone derivatives derived from allyl and homoallyl alcohol backbones has been accomplished via ring closing metathesis reaction. 2-Heteroaryl substituted allyl and homoallyl alcohols have been efficiently resolved through enzymatic method with high ee (97-99%) and known stereochemistry. Antimicrobial and antioxidant activities of target lactones were evaluated.
Sn(II)-Al-Promoted Allylation of Aldehydes with Allyl Chloride in an Aqueous Solvent System
Uneyama, Kenji,Kamaki, Nobuyoshi,Moriya, Akihiko,Torii, Sigeru
, p. 5396 - 5399 (1985)
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Gallium-mediated allylation of carbonyl compounds in water
Wang, Zhiyong,Yuan, Shizhen,Li, Chao-Jun
, p. 5097 - 5099 (2002)
Ga-mediated allylation of aldehydes or ketones in distilled or tap water generated the corresponding homoallyl alcohols in high yields without the assistance of either acidic media or sonication.
Magnesium-cadmium chloride, a bimetallic catalyst system for the allylation of aldehydes with allyl bromide: An efficient protocol for the synthesis of homoallylic alcohols
Venkat Narsaiah,Ramesh Reddy,Gopala Rao,Vijay Kumar,Prakasham,Subba Reddy, Basi V.,Yadav, Jhillu S.
, p. 3461 - 3464 (2008)
A simple and efficient procedure for the allylation of aldehydes has been developed using the magnesium-cadmium chloride reagent system. This bimetallic catalytic system works well in a tetrahydrofuran-water solvent medium. A variety of aldehydes undergo smooth nucleophilic addition with allyl bromide to afford the corresponding homoallylic alcohols in excellent yields. All the reactions were performed at room temperature. Georg Thieme Verlag Stuttgart.
Allylation reactions of aromatic aldehydes with antimony in aqueous media under ultrasonic irradiation
Bian, Yan-Jiang,Zhao, Hong-Mei,Yu, Xu-Guang
, p. 2370 - 2377 (2009)
The allylation reactions of aromatic aldehydes with allyl bromide were carried out in 89-98% yield with Sb-H2O-KF-CH3OH under ultrasound irradiation at rt for 2.5h. The reactions in the same system gave allylic alcohols in 30-69% yie
Water-Compatible Synthesis of 2-Trifluoromethyl-1,3-Dioxanes
Becerra-Figueroa, Liliana,Tiniakos, Alexander F.,Prunet, Jo?lle,Gamba-Sánchez, Diego
, p. 6929 - 6932 (2018)
A water-compatible method for the diastereoselective synthesis of 2-trifluormethyl-1,3-dioxanes is described. The reaction proceeds under mild reaction conditions using simple inorganic bases; it has a very good substrate scope and can be performed with different Michael acceptors. Additionally, the reaction products can be further functionalized, showing an excellent perspective for future applications.
Allylation reactions of aromatic aldehydes and ketones with lithium in THF under ultrasonic irradiation
Bian, Yan-Jiang,Zhang, Jian-You,Li, Ji-Tai
, p. 162 - 163 (2007)
The allylation reactions of aromatic aldehydes and ketones were carried out in 69-90% yield using Li-THF system under ultrasound irradiation at r.t. for 40 min. The reactions of the same system with stirring gave homoallyl alcohols in 49-67% yield at r.t.
Practical approach for catalytic asymmetric allylation of aldehydes with a chiral bidentate titanium(IV) complex
Kii, Satoshi,Maruoka, Keiji
, p. 1935 - 1939 (2001)
A new, chiral bidentate Ti(IV) complex of type 1 was successfully designed and can be utilized for simultaneous coordination to aldehyde carbonyls, thereby allowing the precise enantioface discrimination of such carbonyls for a new catalytic, practical en
Lanthanum trichloride: A simple and efficient catalyst for allylation of aldehydes with allyltributylstannane
Reddy, G. S. Satyanarayana,Sammaiah,Sharada
, p. 3905 - 3911 (2009)
Aldehydes undergo smooth nucleophilic addition with allyltributyl-stannane in the presence of lanthanum trichloride to afford the corresponding homoallylic alcohols in excellent yields. All the reaction conditions were carried out in acetonitrile solvent at room temperature. In all the cases, the catalyst was used in a catalytic amount (10% mol). Copyright Taylor & Francis Group, LLC.
Addition of organochromium reagents to heteroaryl aldehydes. Synthesis of heteroaryl substituted bis-allyl ethers and homoallyl ethers
Servi,Topaloglu
, p. 22 - 28 (2004)
Heteroaryl substituted allyl and homoallyl alcohols were synthesised with two different method. Synthesis of bis-allyl ethers and homoallyl ethers were carried out via reaction of allyl bromide with allyl alcohols and homoallyl alcohols, respectively. [2.3]-Wittig Rearrangement reactions of heteroaryl substituted bis-allyl ethers were investigated using GC/MS techniques. In these reactions two unexpected products were isolated in high yield.
Bismuth triflate catalyzed allylation of aldehydes with allylstannane under microwave assistance
Ollevier, Thierry,Li, Zhiya
, p. 5665 - 5668 (2007)
In the presence of a catalytic amount of bismuth triflate and under microwave irradiation, mixtures of aldehyde and allyl-stannane afforded smoothly the corresponding homoallylic alcohol. A wide variety of aldehydes were treated under these conditions. The reactions proceeded rapidly and afforded smoothly the corresponding homoallylic alcohol in good to very good yields using catalytic amounts of Bi(OTf)3·4H2O (0.5mol-%) and under microwave irradiation for a short time. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Chiral Synthesis via Organoboranes. 36. Exceptionally Enantioselective Allylborations of Representative Heterocyclic Aldehydes at -100 deg C under Salt-Free Conditions
Racherla, Uday S.,Liao, Yi,Brown, Herbert C.
, p. 6614 - 6617 (1992)
Chiral terpenyl-based allylborane reagents (Ter2*BCH2CH=CH2, 1-3) undergo facile condensation with representative heterocyclic aldehydes (HetCHO) at -100 deg C (in the absence of Mg2+ salts) and afford the corresponding homoallylic alcohols (HetCH*(OH)CH2CH=CH2, 12-19) in enantiomeric purities approaching 100percent ee.A new workup procedure involving 8-hydroxyquinoline (8-HQ) has been utilized for the convenient isolation of the product alcohols.
Bispalladacycle Catalyzed Nucleophilic Enantioselective Allylation of Aldehydes by Allylstannanes
Frey, Wolfgang,Heberle, Martin,Legendre, Sarah,Peters, René,Wannenmacher, Nick,Weber, Manuel
, (2022/03/08)
Enantiopure homoallylic secondary alcohols are very important synthetic building due to the versatility of the hydroxyl and olefin moieties. A key strategy to prepare them is by nucleophilic allylation of aldehydes. A large number of catalyst concepts emerged that allow for high enantioselectivity. Still, in many target-oriented syntheses of complex structures stoichiometric methods are preferred over catalytic ones. The need for high catalyst loadings and long reaction times, plus unsatisfying reproducibility and substrate scopes are reasons for that. In the present study we report the first palladium catalysts capable of controlling asymmetric nucleophilic allylations of aldehydes with allyltributyltin. TONs up to 620 were achieved, which is significantly higher than for any other reported catalyst. The method is also tolerating electronically and sterically unfavorable substrates. We show that a transmetallation occurs, favoring an η1-allyl coordination mode with the bispalladacycles. In contrast, for the corresponding monopalladacycle an unproductive η3 coordination is dominant.
Nickel-Catalyzed Reductive Allylation of Aldehydes with Allyl Acetates
Suzuki, Hiroyuki,Yamaguchi,Itoh, Akichika
, p. 1489 - 1494 (2020/12/13)
Carbonyl allylation reactions constitute an important step in the formation of carbon-carbon reactions, and involve various related reactions that chiefly use allylmetal reagents. This report presents a nickel-catalyzed carbonyl allylation reaction using allyl acetate, which produces homoallyl alcohols in moderate to good yields, as an efficient methodology under reductive coupling conditions.
Indium-mediated allylation of carbonyl compounds in deep eutectic solvents
González-Gallardo, Nerea,Saavedra, Beatriz,Guillena, Gabriela,Ramón, Diego J.
, (2021/08/26)
This study describes, for the first time, the in situ generation of indium organometallic reagents in environmentally friendly deep eutectic solvents (DESs). The allylation process of different carbonyl compounds is achieved mediated by indium metal and u
