164527-51-9Relevant academic research and scientific papers
Chemo-, regio- and stereoselective heck arylation of allylated malonates: Mechanistic insights by ESI-MS and synthetic application toward 5-arylmethyl-γ-lactones
Oliveira, Caio C.,Marques, Marcelo V.,Godoi, Marla N.,Regiani, Thas,Santos, Vanessa G.,Santos, Emerson A.F. Dos,Eberlin, Marcos N.,S, Marcus M.,Correia, Carlos R.D.
supporting information, p. 5180 - 5183 (2014/12/11)
We describe herein a general method for the controlled Heck arylation of allylated malonates. Both electron-rich and electron-poor aryldiazonium salts were readily employed as the aryl-transfer agents in good yields and in high chemo-, regio-, and stereoselectivity without formation of decarboxylated byproducts. Reaction monitoring via ESI-MS was used to support the formation of chelated Pd species through the catalytic cycle. Additionally, some Heck adducts were successfully used in the total synthesis of pharmacologically active γ-lactones.
Ferrocenyliminophosphites as easy-to-modify ligands for asymmetric catalysis
Gavrilov, Konstantin N.,Maksimova, Marina G.,Zheglov, Sergey V.,Bondarev, Oleg G.,Benetsky, Eduard B.,Lyubimov, Sergey E.,Petrovskii, Pavel V.,Kabro, Anzhelika A.,Hey-Hawkins, Evamarie,Moiseev, Sergey K.,Kalinin, Valery N.,Davankov, Vadim A.
, p. 4940 - 4947 (2008/03/14)
Several N,P bidentate phosphite-type ligands derived from readily available ferrocene-based iminoalcohols were successfully used in Rh-catalysed hydrogenations and Pd-catalysed allylic substitutions of a variety of substrates. Moderate-to-high catalytic a
Gold(I)-catalyzed [2 + 2]-cycloaddition of allenenes
Luzung, Michael R.,Mauleon, Pablo,Toste, F. Dean
, p. 12402 - 12403 (2008/09/17)
A cationic phosphinegold(I)-catalyzed intramolecular [2 + 2]-cycloaddition between an allene and an alkene to form alkylidene?cyclobutanes is described. Additionally, the reported cycloisomerization reaction provides access to enantioenriched bicyclo-[3.2.0] structures using chiral biarylphosphinegold(I) complexes as catalysts. Copyright
Ir-catalyzed asymmetric allylic alkylation using chiral diaminophosphine oxides: DIAPHOXs. Formal enantioselective synthesis of (-)-paroxetine
Nemoto, Tetsuhiro,Sakamoto, Tatsurou,Fukuyama, Takashi,Hamada, Yasumasa
, p. 4977 - 4981 (2008/02/09)
An Ir-catalyzed asymmetric allylic alkylation using chiral diaminophosphine oxide is described. Asymmetric allylic alkylation of terminal allylic carbonates proceeded using 5 mol % of Ir catalyst, 5 mol % of DIAPHOX 1i, 10 mol % of NaPF6, 10 mo
Recoverable resin-supported pyridylamide ligand for microwave-accelerated molybdenum-catalyzed asymmetric allylic alkylations: Enantioselective synthesis of baclofen
Belda, Oscar,Lundgren, Stina,Moberg, Christina
, p. 2275 - 2278 (2007/10/03)
(Matrix presented) The syntheses of a series of 4-monosubstituted pyridylamides and a resin-supported pyridylamide are described. The ligands were evaluated in the microwave-accelerated molybdenum-catalyzed asymmetric allylic alkylation. The reaction affo
High enantioselectivity in rhodium-catalyzed allylic alkylation of 1-substituted 2-propenyl acetates
Hayashi, Tamio,Okada, Atsushi,Suzuka, Toshimasa,Kawatsura, Motoi
, p. 1713 - 1715 (2007/10/03)
(Matrix presented) Rhodium-catalyzed asymmetric allylic alkylation of 1-substituted 2-propenyl acetates with dimethyl malonate proceeded with high enantioselectivity in the presence of cesium carbonate as a base and a rhodium catalyst generated from Rh(dp
Substituted pyridylamide ligands in microwave-accelerated Mo(0)-catalysed allylic alkylations
Belda, Oscar,Moberg, Christina
, p. 1601 - 1606 (2007/10/03)
Novel 4- and 6-substituted bis-pyridylamides were prepared by microwave accelerated nucleophilic substitution of the 4- and 6-halo substituted derivatives of the parent ligand 1a. The ligands were used in the asymmetric allylation of cinnamyl carbonate catalysed by Mo(O) in which the 4-chloro- and 4-pyrrolidyl substituted ligand derivatives exhibited high regioselectivity (74:1 and 88:1, respectively) and enantioselectivity (96% ee), whereas 6-substituted ligands afforded no product under the same conditions. Other allylic substrates were used to explore the generality of the procedure.
Regiocontrol and Stereoselectivity in Tungsten-Bipyridine Catalysed Allylic Alkylation
Lehmann, Juerg,Lloyd-Jones, Guy C.
, p. 8863 - 8874 (2007/10/03)
Tungsten-bipyridine complexes, generated in situ, catalyse the allylic alkylation of isocinnamyl methyl carbonate by dimethyl sodiomalonate with complete syn-stereoselectivity.When para substituted aryl-allyl methyl carbonates are employed, the regioselectivity correlates with Swain-Lupton parameters.Cross-over experiments demonstrate that the reactions do not proceed via the conventional 0> -> II allyl>+ -> 0 allyl-Nu> catalytic cycle.
