18169-40-9Relevant academic research and scientific papers
Three-component reactions of CF3-substituted boranes, ethyl diazoacetate and imines
Elkin, Pavel K.,Levin, Vitalij V.,Dilman, Alexander D.,Struchkova, Marina I.,Arkhipov, Dmitry E.,Korlyukov, Alexander A.
, p. 6216 - 6218,3 (2012)
Aryl(methoxy)(trifluoromethyl)boranes, generated in situ, readily react with ethyl diazoacetate and N-(4- methoxyphenyl)imines to give derivatives of β-amino acids. In this process, the electron-deficient borane reacts with the diazo compound followed by trapping of the intermediate boron enolate by the imine. The final products are predominantly produced as syn isomers.
Improving C=N bond reductions with (Cyclopentadienone)iron complexes: Scope and limitations
Cettolin, Mattia,Bai, Xishan,Lübken, Dennis,Gatti, Marco,Facchini, Sofia Vailati,Piarulli, Umberto,Pignataro, Luca,Gennari, Cesare
supporting information, p. 647 - 654 (2018/10/24)
Herein, we broaden the application scope of (cyclo-pentadienone)iron complexes 1 in C=N bond reduction. The catalytic scope of pre-catalyst 1b, which is more active than the “Kn?lker complex” (1a) and other members of its family, has been expanded to the catalytic transfer hydrogenation (CTH) of a wider range of aldimines and ketimines, either pre-isolated or generated in situ. The kinetics of 1b-promoted CTH of ketimine S1 were assessed, showing a pseudo-first order profile, with TOF = 6.07 h–1 at 50 % conversion. Moreover, the chiral complex 1c and its analog 1d were employed in the enantioselective reduction of ketimines and reductive amination of ketones, giving fair to good yields and moderate enantioselectivity.
Reactivity of 3-Oxo-β-lactams with Respect to Primary Amines—An Experimental and Computational Approach
Piens, Nicola,Goossens, Hannelore,Hertsen, Dietmar,Deketelaere, Sari,Crul, Lieselotte,Demeurisse, Lotte,De Moor, Jelle,Van den Broeck, Elias,Mollet, Karen,Van Hecke, Kristof,Van Speybroeck, Veronique,D'hooghe, Matthias
, p. 18002 - 18009 (2017/12/13)
The reactivity of 3-oxo-β-lactams with respect to primary amines was investigated in depth. Depending on the specific azetidin-2-one C4 substituent, this reaction was shown to selectively produce 3-imino-β-lactams (through dehydration), α-aminoamides (thr
Paclitaxel Biosynthesis: Adenylation and Thiolation Domains of an NRPS TycA PheAT Module Produce Various Arylisoserine CoA Thioesters
Muchiri, Ruth,Walker, Kevin D.
, p. 1415 - 1425 (2017/03/23)
Structure-activity relationship studies show that the phenylisoserinyl moiety of paclitaxel (Taxol) is largely necessary for the effective anticancer activity. Several paclitaxel analogues with a variant isoserinyl side chain have improved pharmaceutical
Enantioselective Synthesis of Hemiaminals via Pd-Catalyzed C-N Coupling with Chiral Bisphosphine Mono-oxides
Li, Hongming,Belyk, Kevin M.,Yin, Jingjun,Chen, Qinghao,Hyde, Alan,Ji, Yining,Oliver, Steven,Tudge, Matthew T.,Campeau, Louis-Charles,Campos, Kevin R.
supporting information, p. 13728 - 13731 (2016/01/15)
A novel approach to hemiaminal synthesis via palladium-catalyzed C-N coupling with chiral bisphosphine mono-oxides is described. This efficient new method exhibits a broad scope, provides a highly efficient synthesis of HCV drug candidate elbasvir, and has been applied to the synthesis of chiral N,N-acetals.
Decarboxylative Mannich reactions
Boehm, Maximillian,Proksch, Kerstin,Mahrwald, Rainer
supporting information, p. 1046 - 1049 (2013/03/14)
p-Methoxyphenylimines obtained from enolizable aldehydes react in the absence of catalysts at room temperature with β-keto carboxylic acids through a decarboxylative Mannich reaction. The Mannich products were obtained with a high degree of anti selectivity. By use of chiral oxygen-containing aldehydes, operationally simple access to aminohydroxylated polyketide substructures is possible. The results of catalyst-free, decarboxylative Mannich reactions of enolizable imines are described. When the reaction is performed with imines obtained from chiral aldehydes, access to optically pure Mannich products is possible. Copyright
The use of samarium or sodium iodide salts as an alternative for the aza-Henry reaction
Rodríguez-Solla, Humberto,Concellón, Carmen,Alvaredo, Noemí,Soengas, Raquel G.
experimental part, p. 1736 - 1744 (2012/03/10)
A novel reaction of bromonitromethane with a variety of imines in very mild conditions promoted by SmI2 and NaI to afford nitroamines or bromonitroamines is described. When these reactions were performed on sugar-based imines, the corresponding
A modified and highly useful protocol for the Bronsted acid catalyzed, enantioselective, vinylogous Mannich reaction with aliphatic aldimines
Abels, Falko,Schneider, Christoph
experimental part, p. 4050 - 4058 (2012/01/06)
Highly enantioselective as well as diastereoselective catalytic vinylogous Mannich reactions have been accomplished for the first time with aliphatic straight-chain aldimines and O,O-silylketene acetals and furnish valuable synthetic building blocks in hi
Nickel-catalyzed multi-component connection reaction of isoprene, aldimines (lactamines), and diphenylzinc
Kojima, Keisuke,Kimura, Masanari,Ueda, Satoshi,Tamaru, Yoshinao
, p. 7512 - 7520 (2007/10/03)
Ni(acac)2 catalyzes the four-component connection reaction of diphenylzinc, isoprene, aromatic aldehydes, and aromatic amines in this order and provides stereochemically homogeneous (E)-1-arylamino-1-aryl-3-methyl-5-phenyl-3-pentenes (1) in excellent yields. Aliphatic aldehydes react similarly and give (E)-1-arylamino-1-alkyl-3-methyl-5-phenyl-3-pentenes (1) in slightly reduced yields. When the alkyl groups are bulky, in addition to 1 are formed (E)-1-arylamino-1-alkyl-4-methyl-5-phenyl-3-pentenes (1′) as the minor products. Lactamines prepared in situ from five- and six-membered lactols and aromatic amines are more reactive than alkyl aldehyde aldimines and furnish (E)-4-arylamino-6-methyl-8-phenyl-6-octen-1-ols (4) and (E)-5-arylamino-7-methyl-9- phenyl-7-nonen-1-ols (5), respectively, in good yields with excellent E-stereoselectivity.
