25201-44-9Relevant articles and documents
Cu-catalyzed chemoselective preparation of 2-(pinacolato)boron-substituted allylcopper complexes and their insitu site-, diastereo-, and enantioselective additions to aldehydes and ketones
Meng, Fanke,Jang, Hwanjong,Jung, Byunghyuck,Hoveyda, Amir H.
, p. 5046 - 5051 (2013)
Sustainable, efficient, selective: A three-component, single-vessel Cu-catalyzed method for chemo-, diastereo-, and enantioselective conversion of B2(pin)2, monosubstituted allenes, and aldehydes or ketones to 2-B(pin)-substituted homoallylic alkoxides is described. Subsequent functionalization delivers valuable products in up to >98:2 d.r. and 97:3 e.r. (see scheme). Copyright
Formation and direct detection of non-conjugated triplet 1,2-biradical from β,γ-vinylarylketone
Sriyarathne, H. Dushanee M.,Thenna-Hewa, Kosala R.S.,Scott, Tianeka,Gudmundsdottir, Anna D.
, p. 1707 - 1714 (2015)
Laser flash photolysis of 2-methyl-1-phenylbut-3-en-1-one (1) conducted at irradiation wavelengths of 266 and 308nm results in the formation of triplet 1,2-biradical 2 that has max at 370 and 480nm. Biradical 2 is formed with a rate constant of 1.1×107s-1 and decays with a rate constant of 2.3×105s-1. Isoprene-quenching studies support the notion that biradical 2 is formed by energy transfer from the triplet-excited state of the ketone chromophore of 1. Density functional theory calculations were used to verify the characterization of triplet biradical 2 and validate the mechanism for its formation. Thus, it has been demonstrated that intramolecular sensitization of simple alkenes can be used to form triplet 1,2-biradicals with the two radical centres localized on the adjacent carbon atoms.
Allylation of carbonyl compounds in the presence of catalytic electrogenerated zinc. Unusual regioselectivity with a trifluorinated analog of prenyl bromide
Gosmini,Rollin,Perichon,Wakselman,Tordeux,Marival
, p. 6027 - 6034 (1997)
A mild and effective method of electrochemical zinc activation based on the cathodic reduction of a catalytic amount of ZnBr2 in acetonitrile is applied to the coupling of a trifluorinated analog of prenyl bromide with carbonyl compounds and af
Regioreversed Addition of But-2-enyltributylstannane to Aldehydes in the Presence of Aluminium Chloride-Propan-2-ol
Yamamoto, Yoshinori,Maeda, Norihiko,Maruyama, Kazuhiro
, p. 742 - 743 (1983)
The reaction of but-2-enyltributylstannane with certain aldehydes in the presence of AlCl3-PriOH produces the α-adduct (3) either predominantly or exclusively, while the reaction in the presence of ordinary Lewis acids, such as TiCl4, SnCl4, an
Nickel-catalyzed indium(I)-mediated double addition of aldehydes to 1,3-dienes
Hirashita, Tsunehisa,Kambe, Shinya,Tsuji, Hiromitsu,Araki, Shuki
, p. 2595 - 2597 (2006)
In the presence of InI, Ni(acac)2 and PPh3, several 1,3-dienes were reacted with two molecules of aldehyde to give the corresponding 1,4- and 1,6-diols. The regioselectivity of the 1,4-/1,6-diol was efficiently regulated by the addit
Enantioselective allylation of aldehydes promoted by chiral sulfur reagents
Melo, Rosanne P.A.,Vale, Juliana A.,Zeni, Gilson,Menezes, Paulo H.
, p. 1829 - 1831 (2006)
The addition of allylzinc bromide to aldehydes was studied with different chiral sulfur compounds acting as a catalyst. Yield differences and enantiomeric excesses were observed.
Kinetic Resolution of α-Silyl-Substituted Allylboronate Esters via Chemo- and Stereoselective Allylboration of Aldehydes
Park, Jinyoung,Jung, Yongsuk,Kim, Jeongho,Lee, Eunsung,Lee, Sarah Yunmi,Cho, Seung Hwan
supporting information, p. 2371 - 2376 (2020/12/01)
We describe the kinetic resolution of α-silyl-substituted allylboronate esters via chiral phosphoric acid-catalyzed chemo-, diastereo- and enantioselective allylboration of aldehydes. This process provides two synthetically versatile enantioenriched compo
Catalytic Allylation of Aldehydes Using Unactivated Alkenes
Tanabe, Shun,Mitsunuma, Harunobu,Kanai, Motomu
supporting information, p. 12374 - 12381 (2020/07/14)
Simple feedstock organic molecules, especially alkenes, are attractive starting materials in organic synthesis because of their wide availability. Direct utilization of such bulk, inert organic molecules for practical and selective chemical reactions, however, remains limited. Herein, we developed a ternary hybrid catalyst system comprising a photoredox catalyst, a hydrogen-atom-transfer catalyst, and a chromium complex catalyst, enabling catalytic allylation of aldehydes with simple alkenes, including feedstock lower alkenes. The reaction proceeded under visible-light irradiation at room temperature and with high functional group tolerance. The reaction was extended to an asymmetric variant by employing a chiral chromium complex catalyst.
