160115-23-1Relevant articles and documents
Aluminium - SALEN complex: a new catalyst for the enantioselective Michael reaction
Iha, S. C.,Joshi, N. N.
, p. 2463 - 2466 (2001)
A new heterobimetallic complex prepared from a chiral SALEN ligand and Red-Al(R) was found to catalyse the Michael reaction between various dialkyl malonates and cycloalkenones to give products in high yields with e.e. of up to 58 percent.
Mechanism of enantioselective C-C bond formation with bifunctional chiral Ru catalysts: NMR and DFT study
Gridnev, Ilya D.,Watanabe, Masahito,Wang, Hui,Ikariya, Takao
, p. 16637 - 16650 (2010)
The mechanism of Michael addition reactions of 1,3-dicarbonyl compounds to cyclic enones catalyzed by bifunctional Ru catalysts bearing N-sulfonylated (R,R)-DPEN ligands (DPEN = (R,R)-1,2-diphenylethylenediamine) was studied by NMR and DFT computational a
Asymmetric Michael reactions of α-substituted acetates with cyclic enones catalyzed by multifunctional chiral Ru amido complexes
Ikariya, Takao,Wang, Hui,Watanabe, Masahito,Murata, Kunihiko
, p. 1377 - 1381 (2004)
Well-defined 16-electron chiral Ru amido complexes, Ru[(R,R)-diamine](η6-arene), efficiently catalyze asymmetric Michael additions of Michael donors to cyclic enones to give adducts in high yields and with excellent ee's. β-Ketoesters or nitroa
Calcium-BINOL: A novel and efficient catalyst for asymmetric Michael reactions
Kumaraswamy,Sastry,Jena, Nivedita
, p. 8515 - 8517 (2001)
A new calcium-BINOL catalyst has been developed for asymmetric Michael addition reactions of enones and enals. This inexpensive monometallic catalyst functions not only as a Lewis acid but also acts as a Br?nsted base.
Asymmetric michael addition of dimethyl malonate to 2-cyclopenten-1-one catalyzed by a heterobimetallic complex
Fastuca, Nicholas J.,Wong, Alice R.,Mak, Victor W.,Reisman, Sarah E.
, p. 327 - 338 (2021/04/05)
A. Preparation of GaNa-(S)-BINOL((S)-2) Solution (0.05 M).2 A flame-dried 1L, three-necked round-bottomed flask with 24/40 joints and a 1.5 Teflon coated egg-shaped magnetic stir bar is brought into a nitrogen filled glovebox (Note 2). The flask is charged with gallium (III) chloride (5.0 g, 28.4 mmol, 1.0 equiv) (Notes 3 and 4). The flask is sealed with three rubber septa (one of which is fitted with an internal temperature probe) brought out of the glovebox, and put under positive pressure of nitrogen via a needle attached to a nitrogen line. Another flame-dried 1L, three-necked round-bottomed flask with 24/40 joints and a 1.5 Teflon coated egg-shaped magnetic stir bar is charged with (S)-(-)-1,1'-bi(2-naphthol) ((S)-BINOL, (S)-1) (16.26 g, 56.8 mmol, 2.0 equiv) (Note 5). The flask is sealed with three rubber septa (one of which is fitted with a thermometer) and evacuated and backfilled with nitrogen three times (5 minutes under vacuum per cycle). A flame-dried 500 mL round-bottomed flask with a 24/40 joint and a 1 Teflon coated egg-shaped magnetic stir bar is charged with sodium tert -butoxide (10.92 g, 113.6 mmol, 4.0 equiv) (Note 6). The flask is sealed with a rubber septum and evacuated and backfilled with nitrogen three times (5 minutes under vacuum per cycle).
Rendering classical hydrophilic enantiopure Werner salts [M(en)3]: N + n X- lipophilic (M/ n = Cr/3, Co/3, Rh/3, Ir/3, Pt/4); New chiral hydrogen bond donor catalysts and enantioselectivities as a function of metal and charge
Alvi, Scheherzad,Ganzmann, Carola,Gladysz, John A.,Hooda, Karan R.,Maximuck, William J.
, p. 3680 - 3691 (2020/04/03)
Known hydrophilic halide salts of the title compounds are converted to new lipophilic BArf- (B(3,5-C6H3(CF3)2)4-) salts. These are isolated as hydrates (Λ- or Δ-[M(en)
Mapping the Surface Groups of Amine-Rich Carbon Dots Enables Covalent Catalysis in Aqueous Media
Amato, Francesco,Bonchio, Marcella,Companyó, Xavier,Dell'Amico, Luca,Filippini, Giacomo,Prato, Maurizio,Ragazzon, Giulio,Rosso, Cristian,Vega-Pe?aloza, Alberto
supporting information, p. 3022 - 3037 (2020/11/03)
Carbon nanodots stand as the missing link between the molecular and the nanoscale world, owing to the unique molecular-like behavior emerging from their synthetic precursors. A converging set of analytical and spectroscopic data yields a precise inventory
Helical foldamer-catalyzed enantioselective 1,4-addition reaction of dialkyl malonates to cyclic enones
Umeno, Tomohiro,Ueda, Atsushi,Doi, Mitsunobu,Kato, Takuma,Oba, Makoto,Tanaka, Masakazu
supporting information, (2019/11/13)
The introduction of a five-membered ring α,α-disubstituted α-amino acid into L-Leu-based heptapeptides preferentially induced right-handed (P) helical structures. Using 5 ～ 20 mol% of a single helical foldamers-catalyst, enantioselective 1,4-addition reactions of dialkyl malonates to cycloalk-2-enones (5 ～ 7 rings) proceeded to give chiral 3-substituted cycloalkanones with 94 ～ 99% ee in moderate chemical yields, regardless of the ring size of substrates.
Enzyme-Promoted Direct Asymmetric Michael Reaction by Using Protease from Streptomyces griseus
Wu, Ling-Ling,Li, Ling-Po,Xiang, Yang,Guan, Zhi,He, Yan-Hong
, p. 2209 - 2214 (2017/07/24)
The direct asymmetric Michael addition of malonates and enones was promoted by protease from Streptomyces griseus for the first time. Yields of up to 84% with enantioselectivities of up to 98% enantiomeric excess (ee) were achieved under optimized conditi
Bifunctional Ligand-Assisted Catalytic Ketone α-Alkenylation with Internal Alkynes: Controlled Synthesis of Enones and Mechanistic Studies
Mo, Fanyang,Lim, Hee Nam,Dong, Guangbin
supporting information, p. 15518 - 15527 (2015/12/26)
Here, we describe a detailed study of the rhodium(I)-catalyzed, bifunctional ligand-assisted ketone α-C-H alkenylation using internal alkynes. Through controlling the reaction conditions, conjugated enamines, α,β- or β,γ-unsaturated ketones, can be selectively accessed. Both aromatic and aliphatic alkynes can be employed as coupling partners. The reaction conditions also tolerate a broad range of functional groups, including carboxylic esters, malonates, secondary amides, thioethers, and free alcohols. In addition, excellent E-selectivity was observed for the tetra-substituted alkene when forming the α,β-unsaturated ketone products. The mechanism of this transformation was explored through control experiments, kinetic monitoring, synthesizing the rhodium-hydride intermediates and their reactions with alkynes, deuterium-labeling experiments, and identification of the resting states of the catalyst.
