869902-41-0Relevant academic research and scientific papers
Magnetically recyclable palladium nanoparticles (Fe3O4-Pd) for oxidative coupling between amides and olefins at room temperature
Pal, Chandan Kumar,Sahu, Swagatika,Sahu, Ranjan Kumar,Singh, Rajesh Kumar,Jena, Ashis Kumar
, (2019/06/21)
A convenient method for the synthesis of magnetically recyclable palladium nanoparticles (Fe3O4-Pd) is described. The catalytic application of the Fe3O4-Pd nanoparticles was explored for the first time in oxidat
Copper-Catalyzed Enantioselective Synthesis of β-Boron β-Amino Esters
López, Aurora,Clark, Timothy B.,Parra, Alejandro,Tortosa, Mariola
supporting information, p. 6272 - 6275 (2017/12/08)
In this report, the enantioselective, copper-catalyzed borylation of β-amidoacrylates is disclosed. A broad variety of biologically important α-aminoboronates has been prepared with consistently high levels of enantiocontrol using an inexpensive copper catalyst and a commercially available chiral ligand. The method can be applied to the synthesis of novel boron-containing dipeptides and hemiboronates.
Copper-Catalyzed Asymmetric Protoboration of β-Amidoacrylonitriles and β-Amidoacrylate Esters: An Efficient Approach to Functionalized Chiral α-Amino Boronate Esters
Chen, Lili,Zou, Xiaoliang,Zhao, Haonan,Xu, Senmiao
supporting information, p. 3676 - 3679 (2017/07/15)
A copper-catalyzed asymmetric protoboration of both Z-β-amidoacrylonitriles and ethyl E-β-amidoacrylates using bis(pinacolato)diboron has been developed for the first time. The process tolerates a vast array of substrates, delivering a series of stable functionalized chiral α-amino boronate esters in good yields and enantioselectivities under mild reaction conditions. The current method is also applicable for gram-scale synthesis without erosion of enantioselectivity. This work provides an attractive and complementary approach to synthesizing enantioriched chiral α-amino boronate esters.
Stereoselective synthesis of enamides by pd-catalyzed hydroamidation of electron deficient terminal alkynes
Panda, Niranjan,Mothkuri, Raghavender
, p. 9407 - 9412,6 (2012/12/12)
Hydroamidation of electron-deficient terminal alkynes by amides in presence of Pd-catalyst has been exploited for the stereoselective synthesis of Z-enamides. The possible intramolecular hydrogen bonding between the amido proton and carbonyl oxygen of est
New [11C]phosgene based synthesis of [11C]pyrimidines for positron emission tomography
Seki, Koh-Ichi,Nishijima, Ken-Ichi,Sanoki, Kimihito,Kuge, Yuji,Takahashi, Masayuki,Akizawa, Hiromichi,Tamaki, Nagara,Wiebe, Leonard I.,Ohkura, Kazue
experimental part, p. 1307 - 1321 (2010/10/03)
Thymine, 5-FU, and uracil were successfully synthesized through a procedure involving a cyclocondensation of triphosgene with newly developed (α-substituted β-aminoacrylamides intermediates (1a, X= Me; 1b, X= F; 1c, X= H). The radioligands [2-11C]thymine and [2- 11C]5-fluorouracil were synthesized in high radiochemical yields in 16-17 minutes from the end of bombardment by applying the cyclocondensation method with [11C]COCl2.
An efficient approach to the stereocontrolled synthesis of enamides
Villa, Mathew V. J.,Targett, Sarah M.,Barnes, John C.,Whittingham, William G.,Marquez, Rodolfo
, p. 1631 - 1633 (2008/02/02)
A fast, flexible, and efficient approach for the stereocontrolled synthesis of enamides has been developed starting from lactams and amides through the use of imides. This new approach provides access to enamide systems not easily or currently accessible through other approaches.
Hydrogen-bond-directed highly stereoselective synthesis of Z-enamides via Pd-catalyzed oxidative amidation of conjugated olefins
Lee, Ji Min,Ahn, Doo-Sik,Jung, Doo Young,Lee, Junseung,Do, Youngkyu,Kim, Sang Kyu,Chang, Sukbok
, p. 12954 - 12962 (2008/02/10)
An efficient procedure for the preparation of Z-enamides has been developed, involving the reaction of primary amides with conjugated olefins using a Pd/Cu cocatalyst system. It was found that certain additives, such as phosphine oxides and phosphonates, increase the efficiency of the reaction in nonpolar solvents under an oxygen atmosphere, thus producing a variety of Z-enamides in high yields with excellent stereoselectivity under Wacker-type conditions. The oxidative amidation reaction has a broad substrate scope, allowing alkyl, aryl, and vinyl amides to react with olefins conjugated with ester, amide, phosphonate, and ketone groups. The notable preference for the formation of Z-enamides is presumably due to the presence of an intramolecular hydrogen bond between the amido proton and the carbonyl oxygen. The energy difference between two plausible σ-alkylamidopalladium intermediates, leading to Z- and E-isomeric enamide products, respectively, was calculated to be 4.18 kcal/mol. The β-hydride elimination step is assumed to be a stereochemistry-determining step in the overall oxidative amidation process, with the energy level for the transition state leading to the Z-enamide being 5.35 kcal/mol lower than that leading to the E-isomer. The efficiency of photoisomerization between Z- and E-enamides was observed to be largely dependent on the substrates' substituents, and certain E-enamides could be obtained in synthetically useful yields by photoirradiation of Z-isomers. Synthetic application of the present method was successfully demonstrated by a direct formal synthesis of cis-CJ-15,801.
