90172-86-4Relevant academic research and scientific papers
Trimethyl Orthoacetate and Ethylene Glycol Mono-Vinyl Ether as Enolate Surrogates in Enantioselective Iridium-Catalyzed Allylation
Sempere, Yeshua,Carreira, Erick M.
, (2018)
Trimethyl orthoacetate and ethylene glycol mono-vinyl ether are employed in iridium-catalyzed enantioselective allylation reactions. The method documented enables their convenient use as surrogates for silyl ketene acetals and silyl enol ethers to prepare
Studies on the chemoenzymatic synthesis of 3-phenyl-GABA and 4-phenyl-pyrrolid-2-one: The influence of donor of the alkoxy group on enantioselective esterification
Brodzka, Anna,Koszelewski, Dominik,Cwiklak, Malgorzata,Ostaszewski, Ryszard
, p. 427 - 433 (2013/07/19)
A new chemoenzymatic method for the synthesis of enantiomerically pure 3-phenyl-γ-aminobutyric acid 1 and 4-phenyl-pyrrolid-2-one 9 based on the enzymatic kinetic resolution of 3-phenyl-4-pentenoic acid 2 is described herein. Enzymatic resolution of the r
The studies on chemoenzymatic synthesis of Femoxetine
Brodzka, Anna,Koszelewski, Dominik,Ostaszewski, Ryszard
experimental part, p. 96 - 101 (2012/09/25)
The studies on enzymatic kinetic resolution of 3-phenyl-4-pentenoic acid esters were performed. The obtained results demonstrated that the careful choice of biocatalyst and a reaction type are very important for successful enzymatic kinetic resolution. Ki
Iridium-catalyzed enantioselective allylic alkylation of methyl 2-(4-nitrophenylsulfonyl)acetate and subsequent transformations
Xu, Qing-Long,Dai, Li-Xin,You, Shu-Li
supporting information, p. 2275 - 2282 (2012/11/07)
Highly enantioselective allylic alkylation reactions of methyl 2-(4-nitrophenylsulfonyl)acetate were carried out in the presence of an iridium catalytic system. The subsequent transformations of the products including reductive desulfonylation and modifie
Homogeneous gold-catalyzed oxidative carboheterofunctionalization of alkenes
Zhang, Guozhu,Cui, Li,Wang, Yanzhao,Zhang, Liming
supporting information; experimental part, p. 1474 - 1475 (2010/04/04)
(Chemical Equation Presented) Homogeneous carboamination, carboalkoxylation and carbolactonization of terminal alkenes are realized via oxidative gold catalysis, providing expedient access to various substituted Nor O-heterocycles. Deuterium-labeling studies established the anti nature of the alkene functionalization and the indispensible role of Au(I)/Au(III) catalysis. This study constitutes the first example of catalytically converting C(sp 3)-Au bonds into C(sp3)-C(sp2) bonds in a crosscoupling manner and opens new opportunities to study gold alkene catalysis where alkylgold intermediates can be readily functionalized intermolecularly. Copyright
Multicatalytic synthesis of complex tetrahydrofurans involving bismuth(iii) triflate catalyzed intramolecular hydroalkoxylation of unactivated olefins
Kelly, Brendan D.,Allen, Julia M.,Tundel, Rachel E.,Lambert, Tristan H.
supporting information; experimental part, p. 1381 - 1383 (2009/10/02)
A multicatalytic synthesis of complex tetrahydrofurans has been developed involving a Bi(OTf)3-catalyzed nucleophilic addition/ hydroalkoxylation sequence. Complex tetrahydrofuranyl products may be formed rapidly in high yield and with good diastereoselectivity. The demonstrated scope of hydroalkoxylation has also been expanded to include substrates bearing useful functional handles including carboxylate ester, olefin, nitrile, and nitro groups.
Stereoselective cyclization using palladium(II) catalyst via hemiacetal intermediates
Miyazawa, Masahiro,Hirose, Yukari,Narantsetseg, Magsarjav,Yokoyama, Hajime,Yamaguchi, Seiji,Hirai, Yoshiro
, p. 2883 - 2886 (2007/10/03)
A stereoselective palladium-catalyzed cyclization of 3-phenyl-7-hydroxy-5- heptenal was developed. The reaction was carried out to give 2,4,6-trisubstituted tetrahydropyran with highly controlled 4,6-cis stereochemistry.
Predominant 1,2-insertion of styrene in the Pd-catalyzed alternating copolymerization with carbon monoxide
Nozaki,Komaki,Kawashima,Hiyama,Matsubara
, p. 534 - 544 (2007/10/03)
The regioselectivity of styrene insertion to an acyl-Pd bond was studied by NMR in (i) a stoichiomeric reaction and (ii) a copolymerization with CO. In the stoichiometric reaction of styrene with [(CH3CO)Pd-(CH3CN){(R,S)-BINAPHOS}] ·[B{3,5-(CF3)2C6 H3}4], both 1,2-and 2,1-products were given. To mimic the real polymerization conditions, a polyketone-substituted complex [{CH3(CH2CHCH3CO)n}Pd{(R,S)-BINAP HOS}]·[B(3,5-(CF3)2C6 H3)4] (n ≈ 14) was prepared. When this polymer-attached Pd species was treated with styrene, the 1,2-insertion product was the only detectable species. Thus, exclusive 1,2-insertion is demonstrated to be responsible for the styrene-CO copolymerization, in sharp contrast to the predominant 2,1-insertion with conventional nitrogen ligands. Chain-end analysis revealed that β-hydride elimination took place from the 2,1-complex but not from the 1,2-complex. Thus, once 2,1-insertion occurs, rapid β-hydride elimination proceeds to terminate the polymerization, as is common to the other phosphorus-ligand systems. The resulting Pd-H species re-initiates the copolymerization, as was proven by MALDI-TOF mass analysis of the product copolymers.
Allylic alkylation with function-bearing organozinc reagents
Doucet, Henri,Brown, John M.
, p. 995 - 1000 (2007/10/03)
The first palladium-catalysed alkylations of allylic acetates with organozinc reagents bearing functionality are reported.The reaction proceeds well from ethanoate, and propanoates, derived organozinc halides and provides a useful method for transferring these moieties to an allyl fragment.The reaction proceeds through a monophosphine complex; attempts to perform asymmetric syntheses are unsuccessful so far. - Keywords: palladium; coupling; allylic substitution
Aza-Claisen rearrangements initiated by acid-catalyzed Michael addition
Vedejs, Edwin,Gingras, Marc
, p. 579 - 588 (2007/10/02)
The reaction of allylic amines with dimethyl acetylenedicarboxylate is subject to protic acid catalysis and affords 15, the product of Michael addition and aza-Claisen rearrangement. The sequence involves Michael addition of 4c or 19-21 to generate an int
