6846-55-5Relevant academic research and scientific papers
A Ball-Milling-Enabled Reformatsky Reaction
Cao, Qun,Stark, Roderick T.,Fallis, Ian A.,Browne, Duncan L.
, p. 2554 - 2557 (2019/06/17)
An operationally simple one-jar one-step mechanochemical Reformatsky reaction using in situ generated organozinc intermediates under neat grinding conditions has been developed. Notable features of this reaction protocol are that it requires no solvent, no inert gases, and no pre-activation of the bulk zinc source. The developed process is demonstrated to have good substrate scope (39–82 % yield) and is effective irrespective of the initial morphology of the zinc source.
One-Pot Silyl Ketene Acetal-Formation Mukaiyama-Mannich Additions to Imines Mediated by Trimethylsilyl Trifluoromethanesulfonate
Wade Downey,Ingersoll, Jared A.,Glist, Hadleigh M.,Dombrowski, Carolyn M.,Barnett, Adam T.
supporting information, p. 7287 - 7291 (2015/11/25)
In the presence of trimethylsilyl trifluoromethanesulfonate and trialkylamine base, thioesters are readily converted into silyl ketene acetals in situ and undergo Mukaiyama-Mannich addition to N-phenylimines in one pot. The silyl triflate appears to play
Stereodefined homopropargyl amines by tandem nucleophilic addition/fragmentation of dihydropyridone triflates
Tummatorn, Jumreang,Dudley, Gregory B.
supporting information; experimental part, p. 158 - 160 (2011/03/20)
Dihydropyridone (DHPD) triflates undergo nucleophile-triggered fragmentation to provide homopropargyl amine derivatives, the stereochemistry of which is defined by starting from readily available β-amino esters.
Synthesis of N-phenyl β-amino acids via iridium-catalyzed asymmetric hydrogenation using mixed monodentate ligands
Mrsic, Natasa,Panella, Lavinia,Minnaard, Adriaan J.,Feringa, Ben L.,De Vries, Johannes G.
scheme or table, p. 36 - 39 (2011/04/18)
The iridium-catalyzed asymmetric hydrogenation of N-phenyl-β- dehydroamino acid derivatives was examined using monodentate phosphoramidite ligands. The highest yields and enantioselectivities were obtained using a mixed ligand approach with PipPhos L1 and
Hydrogenation of β-N-substituted and β-N,N-disubstituted enamino esters in the presence of iridium(I) catalyst
Hebbache, Hania,Hank, Zakia,Bruneau, Christian,Renaud, Jean-Luc
experimental part, p. 2627 - 2633 (2009/12/06)
Several new β-amino esters were prepared in two simple steps from β-keto ester derivatives and primary and secondary amines under mild conditions. The hydrogenation of various enamino esters was performed at 50°C in the presence of iridium catalysts. The new β-N-substituted amino esters were isolated in high yields. Georg Thieme Verlag Stuttgart.
Natural phosphate modified with lithium nitrate: A new efficient catalyst for the construction of carbon-carbon, carbon-sulfur, and carbon-nitrogen bonds
Zahouily, Mohamed,Mounir, Bahija,Cherki, Hind,Bahlaouan, Bouchaib,Rayadh, Ahmed,Sebti, Said
, p. 1203 - 1217 (2008/02/02)
The addition of small amounts of lithium nitrate to natural phosphate followed by calcination gives a new catalyst Li/NP (weight ratio LiNO3/NP = 1/15). This material showed catalytic activity in the Michael addition of amines, mercaptans, and active methylene compounds to chalcone derivatives with high yields under mild reaction conditions. Li/NP is used as the catalyst for a facile synthesis of -amino acids, -sulfur acids, and 4 H-chromenes under heterogeneous conditions. The usual, undesirable byproducts from the Michael condensation such as 1,2-addition, bis-addition, and polymerization compounds are not observed with this method. The work-up procedure is simplified by simple filtration with the use of Li/NP.
Solvent-free synthesis of β-hydroxy esters and β-amino esters by indium-mediated reformatsky reaction
Chen, Xi'an,Zhang, Changfu,Wu, Huayue,Yu, Xiaochun,Su, Weike,Cheng, Jiang
, p. 3233 - 3239 (2008/09/16)
In a convenient and efficient procedure for the solvent-free synthesis of β-hydroxy esters and β-amino esters, various aldehydes and aldimines undergo a Reformatsky reaction mediated by non-activated indium at room temperature to give the corresponding esters in good to excellent yields. Georg Thieme Verlag Stuttgart.
Synthesis of β-lactams and β-aminoesters via high intensity ultrasound-promoted Reformatsky reactions
Ross, Nathan A.,MacGregor, Robert R.,Bartsch, Richard A.
, p. 2035 - 2041 (2007/10/03)
Reformatsky reactions of an imine, an α-bromoester, zinc dust and a catalytic amount of iodine in dioxane under high intensity ultrasound (HIU) irradiation from an ultrasonic probe are explored. A series of 16 aldimines with varying electronic demands is
The synthesis of β-lactams via a one-pot Reformatsky reaction of imines promoted by Zn/Cp2TiCl2 (cat.)
Chen, Lei,Zhao, Gang,Ding, Yu
, p. 2611 - 2614 (2007/10/03)
In the presence of Zn/Cp2TiCl2 (cat.) α-bromoacetates, γ-bromocrotonates or α-bromomethylacrylates react with imines in one-pot to form β-lactams, 3-vinyl-β-lactams or α-methylene-γ-lactams, respectively, at room temperature without
Selective synthesis of β-amino esters and β-lactams by rhodium-catalyzed reformatsky-type reaction
Kanai, Kazuo,Wakabayashi, Hitoshi,Honda, Toshio
, p. 47 - 51 (2007/10/03)
β-Amino esters and β-lactams are synthesized selectively from aldimines and ethyl bromoacetate by applying a simply modified rhodium-catalyzed Reformatsky-type reaction.
