19781-52-3Relevant academic research and scientific papers
Highly efficient synthesis of the tricyclic core of taxol by cascade metathesis
Letort, Aurelien,Aouzal, Remi,Ma, Cong,Long, De-Liang,Prunet, Joelle
supporting information, p. 3300 - 3303 (2014/07/08)
An efficient enantioselective synthesis of the ABC tricyclic core of the anticancer drug Taxol is reported. The key step of this synthesis is a cascade metathesis reaction, which leads in one operation to the required tricycle if appropriate fine-tuning o
Palladium(II)-Catalyzed Intramolecular Aminocarbonylation of endo-Carbamates under Wacker-Type Conditions
Harayama, Hiroto,Abe, Atsuhiro,Sakado, Tomonori,Kimura, Masanari,Fugami, Keigo,Tanaka, Shuji,Tamaru, Yoshinao
, p. 2113 - 2122 (2007/10/03)
Pd(II)-catalyzed intramolecular aminocarbonylation of olefins bearing many types of nitrogen nucleophiles has been examined under two typical conditions: acidic conditions [conditions A, typically PdCl2 (0.1 equiv) and CuCl2 (3.0 equiv) under 1 atm of CO at room temperature in methanol] and buffered conditions [conditions B, typically PdCl2 (0.1 equiv) and CuCl2 (2.3 equiv) under 1 atm of CO at 30°C in trimethyl orthoacetate]. Among nitrogen nucleophiles, endocarbamates 7 display distinctive reactivity: endo-carbamates 7a-k smoothly undergo intramolecular aminocarbonylation under conditions B to furnish 4-[(methoxycarbonyl)methyl]-2-oxazolidinones 8a-k in good yields, while they would not undergo the expected reaction under conditions A. Other nitrogen nucleophiles (exo-ureas 1, endo-ureas 3, exo-carbamates 5, and exo-tosylamides 9), on the other hand, satisfactorily undergo aminocarbonylation only under conditions A to give rise to 2,4,6, and 10, respectively, in good yields. Under conditions B, they are unreactive and provide either the expected products in poor yields or intractable mixtures of products. On the basis of this contrasting reactivity between endo-carbamates and other nitrogen nucleophiles, the chemoselective aminocarbonylation of 71-o has been achieved; aminocarbonylation takes place at the endo-carbamate moieties to furnish 81-o exclusively under conditions B, and aminocarbonylation occurs at the exo-carbamate, exo-urea, and exo-tosylamide moieties to yield 13a-d exclusively under conditions A.
On the Regioselectivity of Coupling of Substituted Allyl Radicals. Steric Versus FMO Control
Pasto, Daniel J.,L'Hermine, Gael
, p. 3259 - 3272 (2007/10/02)
The photo-induced decomposition of substituted-homoallylic 4-nitrobenzenesulfenates produces substituted allyl radicals which undergo dimerization and coupling with the 4-nitrobenzenethiyl radical.The regioselectivity of the dimerization of the allyl redi
ELECTROSYNTHESIS OF ALCOHOLS FROM ORGANIC HALIDES AND KETONES OR ALDEHYDES
Sibille, Soline,d'Incan, Esther,Leport, Louis,Perichon, Jacques
, p. 3129 - 3132 (2007/10/02)
The electrosynthesis of a wide range of alcohols from organic halides and ketones or aldehydes is achieved under simple and mild conditions in an undivided electrolytic cell using different sacrificial anodes.
ELECTROCHEMICAL ADDITIONS OF THE ALLYL AND THE BENZYL GROUPS OF ALLYL AND BENZYL HALIDES TO ACETONE.
Satoh,Suginome,Tokuda
, p. 1791 - 1794 (2007/10/02)
Electrolysis of allyl chloride and five molar excess of acetone in hexamethylphosphoric triamide containing 0. 5 M tetrabutylammonium perchlorate gave an addition product, 2-methyl-4-penten-2-ol, in a 53% yield. Allyl groups of 1-chloro-2-methyl-2-propene, 1-chloro-2-butene(3), 3-chloro-1-butene(4), 1-chloro-3-methyl-2-butene(5), and 3-chloro-3-methyl-1-butene(6), and benzyl groups of benzyl chloride, benzyl bromide, and 1-chloro-1-phenylethane can similarly be added to acetone by electrolysis to give the corresponding alcohols in fair to good yields. Among these electrochemical reactions, those of 3, 4, 5 and 6 with acetone give respectively two isomeric homoallyl alcohols, one of the isomers is not accessible by the usual chemical reaction between allylic organometallics and acetone.
REACTIONS OF TITANOCENE ALLYLS
Klei, E.,Teuben, J.H.,De Liefde Meijer, H.J.,Kwak, E.J.,Bruins, A.P.
, p. 327 - 339 (2007/10/02)
Cp2Tiη3-allyl and Cp2Tiη3-1-methylallyl react with carbon dioxide, phenylisocyanate, benzalaniline, acetone and acetonitrile to give insertion products which are formed via allyl migration.Normal insertion is observed with 2,6-xylylisocyanide.C
Titanium-promoted Allyl Transfer to Carbon Monoxide and Other Unsaturated Molecules
Klei, Bert,Teuben, Jan H.,Meijer, Henk J. de Liefde
, p. 342 - 344 (2007/10/02)
Carbonylation of Cp2Ti-(?-allyl) yields Cp2Ti(CO)2 and triallylmethanol; reactions of Cp2Ti-(?-allyl) and Cp2Ti-(?-1-methylallyl) with other ligands proceed via insertion or allyl-elimination pathways.
REGIOSELECTIVITY IN ELECTROCHEMICAL ADDITIONS OF THE ALLYL GROUPS IN SUBSTITUTED ALLYL HALIDES TO α,β-UNSATURATED ESTERS OR ACETONE
Satoh, Shohei,Suginome, Hiroshi,Tokuda, Masao
, p. 1895 - 1898 (2007/10/02)
Electrochemical addition of the allyl groups in substituted allyl halides to some α,β-unsaturated esters took place in a regioselective manner at either of their α-, or γ-carbon terminus, whereas regioselectivity in the addition to acetone was found to be controlled by changing a cathode material or an electrolytic potential.
SYNTHESIS OF HOMOALLYL ALCOHOLS BY THE REACTION OF ?-ALLYLDICYCLOPENTADIENYLTITANIUM(III) WITH CARBONYL COMPOUNDS
Sato, Fumie,Iijima, Satoshi,Sato, Masao
, p. 243 - 246 (2007/10/02)
Reaction of ?-allyldicyclopentadienyltitanium(III) complexes, preformed or formed in situ, with aldehydes or ketones proceeds with regiospecificity, high stereoselectivity and chemospecificity, affording, under mild conditions, the corresponding homoallyl alcohols after hydrolysis in excellent yields.
