71787-60-5Relevant academic research and scientific papers
A Catalytic Dual Isomerization/Allylboration Sequence for the Stereoselective Construction of Congested Secondary Homoallylic Alcohols
Liu, Yangbin,Mazet, Clément
, p. 5638 - 5650 (2020/05/19)
A catalytic sequence for the diastereo- and enantioselective preparation of homoallylic alcohols with an adjacent quaternary (stereo)center is reported. The one-pot process relies on the use of a single (achiral or chiral) iridium complex to catalyze the concomitant isomerization of primary allylic alcohols and homoallylboronates into (chiral) aldehydes and allylboronates, respectively. In the same flask, a chiral Br?nsted acid is added next to engage the isomerization products into a stereocontrolled allylboration reaction. Structural variations have been performed on both the allylic alcohols and the homoallylboronates. This mild process affords an array of stereochemically congested and complex chiral secondary homoallylic alcohols in high yield, excellent diastereoselectivity, and usually high enantioselectivity.
Cp2TiCl2-Catalyzed Photoredox Allylation of Aldehydes with Visible Light
Bergamini, Giacomo,Calogero, Francesco,Cozzi, Pier Giorgio,Fermi, Andrea,Gualandi, Andrea,Guazzi, Simone,Mazzarini, Martino
, p. 3857 - 3863 (2020/03/26)
A Barbier-type Cp2TiCl2-mediated (10 mol %) photoredox allylation of aldehydes under irradiation with visible light (blue light-emitting diodes (LEDs), 450 nm) and in the presence of an organic dye (3DPAFIPN, 5 mol %) with allylbromides is described.
Copper-Catalyzed Diamination of Alkenes of Unsaturated Ketohydrazones with Amines
Chen, Manman,Wang, Li-Jing,Ren, Pei-Xing,Hou, Xiao-Ying,Fang, Zhang,Han, Meng-Nan,Li, Wei
supporting information, p. 510 - 513 (2018/02/10)
A convenient copper-catalyzed intra-/intermolecular diamination of β,γ-unsaturated hydrazones has been developed with simple amines as external amine sources. The protocol enables efficient access to various nitrogen-containing pyrazolines under mild reaction conditions.
Transition-metal-free reductive coupling of 1, 3-butadienes with aldehydes catalyzed by dibutyliodotin hydride
Suzuki, Itaru,Uji, Yuki,Kanaya, Shujiro,Ieki, Ryosuke,Tsunoi, Shinji,Shibata, Ikuya
supporting information, p. 5392 - 5394 (2017/11/07)
In this study, the Bu2SnIH-catalyzed direct coupling of 1, 3- dienes with aldehydes was developed. This reaction could be suitable for coupling without the use of transition-metal catalysts. Many types of aldehydes were applied to this reaction. The addition of MeOH promoted the catalytic cycle.
Iminoxyl Radical-Promoted Oxycyanation and Aminocyanation of Unactivated Alkenes: Synthesis of Cyano-Featured Isoxazolines and Cyclic Nitrones
Chen, Fei,Zhu, Fei-Fei,Zhang, Man,Liu, Rui-Hua,Yu, Wei,Han, Bing
supporting information, p. 3255 - 3258 (2017/06/23)
A novel and facile approach to vicinal oxycyanation and aminocyanation of internal unactivated alkenes is developed. This method utilizes the dichotomous reactivity of iminoxyl radical derived from the initiation of β,γ- and γ,δ-unsaturated ketoximes to provide the general difunctionalization of internal alkenes using tert-butyl hydroperoxide (TBHP) as the environmentally friendly oxidant, CuCN as the commercially available cyanating reagent, and pentamethyldiethylenetriamine (PMDETA) as the ligand. By using this protocol, a series of useful cyano-featured isoxazolines and cyclic nitrones were efficiently prepared.
Hydroxyl-directed stereoselective diboration of alkenes
Blaisdell, Thomas P.,Caya, Thomas C.,Zhang, Liang,Sanz-Marco, Amparo,Morken, James P.
, p. 9264 - 9267 (2014/07/21)
An alkoxide-catalyzed directed diboration of alkenyl alcohols is described. This reaction occurs in a stereoselective fashion and is demonstrated with cyclic and acyclic homoallylic and bishomoallylic alcohol substrates. After oxidation, the reaction generates 1,2-diols such that the process represents a method for the stereoselective directed dihydroxylation of alkenes.
Iminoxyl radical-promoted dichotomous cyclizations: Efficient oxyoximation and aminooximation of alkenes
Peng, Xie-Xue,Deng, Yun-Jing,Yang, Xiu-Long,Zhang, Lin,Yu, Wei,Han, Bing
supporting information, p. 4650 - 4653 (2015/01/08)
A novel iminoxyl radical-involved metal-free approach to vicinal oxyoximation and aminooximation of unactivated alkenes is developed. This method utilizes the dichotomous reactivity of the iminoxyl radical to furnish a general difunctionalization on alkenes using simple tert-butyl nitrite (TBN) as the iminoxyl radical initiator as well the carbon radical trap. By using this protocol, oxime featured 4,5-dihydroisoxazoles and cyclic nitrones were facilely prepared from β,γ- and γ,δ-unsaturated ketoximes, respectively.
Dibutyltin oxide catalyzed allyl-transfer reaction from tertiary homoallylic alcohols to aldehydes
Yanagisawa, Akira,Aoki, Takahiro,Arai, Takayoshi
, p. 2071 - 2074 (2008/02/05)
A catalytic allyl-transfer reaction from tertiary homoallylic alcohols to aldehydes was achieved using dibutyltin oxide as a catalyst in toluene under reflux conditions. Various secondary homoallylic alcohols were prepared in high yield (up to 99%). When β-alkylated tertiary homoallylic alcohols were used, branched products were exclusively obtained. Georg Thieme Verlag Stuttgart.
Direct preparation of allylic indium(III) reagents from allylic alcohols via a reductive transmetalation of π-allylnickel(II) with indium(I) iodide
Hirashita, Tsunehisa,Kambe, Shinya,Tsuji, Hiromitsu,Omori, Hideki,Araki, Shuki
, p. 5054 - 5059 (2007/10/03)
InI-mediated direct allylation of carbonyl compounds with allylic alcohols proceeded smoothly with catalytic amounts of Ni(acac)2 and PPh 3 to give the corresponding homoallylic alcohols in high yields. Allylindium compounds were shown to be the real allylating agents in the present system. Substituted allylic alcohols gave branched homoallylic alcohols with syn-selectivity irrespective of the geometry of the starting allylic alcohols, whereas high anti-selectivity was observed when a bulky substituent is present in the allylic alcohols. The outcome of the diastereoselectivity is discussed on the basis of the reaction mechanism, comparing with the corresponding Pd-catalyzed version. Another distinct behavior between the Ni- and Pd-catalyzed allylation was demonstrated in the reaction of hex-1,5-diene-3,4-diol derivatives: the Pd catalyst did not give any coupling product, whereas the Ni-catalyzed InI-mediated reaction with benzaldehyde afforded the 1:1 and 1:2 adduct diols selectively depending on the reaction conditions.
New catalytic cycle for couplings of aldehydes with organochromium reagents
Namba, Kosuke,Kishi, Yoshito
, p. 5031 - 5033 (2007/10/03)
(Chemical Equation Presented) A new catalytic cycle has been developed to effect all three subgroups of Cr-mediated couplings, i.e., (1) Ni/Cr-mediated alkenylation, alkynylation, and arylation, (2) Co/Cr-mediated 2-haloallylation, alkylation, and proparg
