5500-46-9Relevant academic research and scientific papers
XtalFluor-E mediated proto-functionalization of: N -vinyl amides: Access to N -acetyl N, O -acetals
Yi,Gholami,Morrow,Borhan
, p. 9570 - 9574 (2017/11/30)
XtalFluor-E has been extensively used in a broad range of reactions in the past few years. Here we report its use with protic nucleophiles in a catalytic manner for the in situ generation of protons that lead to the proto-functionalization of activated ol
Structure-Dependent Nickel-Catalysed Transposition of N -Allylamides to E- or Z-Enamides
Weber, Felicia,Steinlandt, Philipp S.,Ballmann, Monika,Hilt, Gerhard
, p. 440 - 450 (2016/12/24)
The nickel-catalysed transposition of a carbon-carbon double bond of N-allyl and N-homoallyl amides is described. While the transposition of acyclic amides gave very high Z-selectivity of the enamides, corresponding cyclic N-allyl amides led exclusively t
Pd-Boron-Catalyzed One Carbon Isomerization of Olefins: Water Assisted Process at Room Temperature
Ojha, Devi Prasan,Gadde, Karthik,Prabhu, Kandikere Ramaiah
, p. 4859 - 4865 (2017/05/12)
A palladium-boronate/borane-system -catalyzed isomerization of olefins has been uncovered. An efficient catalytic combination of [Pd(OAc)2]3-boronate-PCy3-enabled olefin isomerization at 80 °C has been investigated. Addition of water to the reaction showed a remarkable improvement and the isomerization occurred at ambient temperature. These catalytic systems function efficiently for the isomerization of functionalized as well as unfunctionalized olefins. The catalytic conditions demonstrate the involvement of both nonhydride and metal-hydride medium and can be switchable with water as an additive.
Isomerization of N-Allyl Amides to Form Geometrically Defined Di-, Tri-, and Tetrasubstituted Enamides
Trost, Barry M.,Cregg, James J.,Quach, Nicolas
supporting information, p. 5133 - 5139 (2017/05/04)
Enamides represent bioactive pharmacophores in various natural products, and have become increasingly common reagents for asymmetric incorporation of nitrogen functionality. Yet the synthesis of the requisite geometrically defined enamides remains problematic, especially for highly substituted and Z-enamides. Herein we wish to report a general atom economic method for the isomerization of a broad range of N-allyl amides to form Z-di-, tri-, and tetrasubstituted enamides with exceptional geometric selectivity. This report represents the first examples of a catalytic isomerization of N-allyl amides to form nonpropenyl disubstituted, tri- and tetrasubstituted enamides with excellent geometric control. Applications of these geometrically defined enamides toward the synthesis of cis vicinal amino alcohols and tetrasubstituted α-borylamido complexes are discussed.
Site-Selective Silylation of Aliphatic C-H Bonds Mediated by [1,5]-Hydrogen Transfer: Synthesis of α-Sila Benzamides
Liu, Pei,Tang, Jinghua,Zeng, Xiaoming
supporting information, p. 5536 - 5539 (2016/11/17)
The first example of site-selective silylation of C(sp3)-H bonds mediated by a [1,5]-hydrogen transfer is reported. This reaction occurs selectively at the α-position of benzamides with a combination of tert-butylmagnesium chloride and a catalytic amount of 4,4′-di-tert-butylbipyridine (dtbpy) ligand and provides a facile route for the creation of biologically interesting α-sila benzamides. Late-stage functionalization of the incorporated silyl moieties facilitates the synthesis of N-formyl, cis-enamine, β-hydroxyl, amino, and pyrrole-containing derivatives.
Nickel-Catalyzed Synthesis of Enamides and Enecarbamates via Isomerization of Allylamides and Allylcarbamates
Halli, Juliette,Kramer, Philipp,Bechthold, Maren,Manolikakes, Georg
supporting information, p. 3321 - 3324 (2015/11/03)
A single-component, air-stable nickel precatalyst can catalyze the isomerization of allylamides for the synthesis of enamides. The scope of the reaction encompasses various substituted allylamides and allylcarbamates as well as homoallylamides. The reaction can be performed on a multigram-scale without specialized glove-box equipment or Schlenk techniques.
Relay catalysis by a metal-complex/bronsted acid binary system in a tandem isomerization/carbon-carbon bond forming sequence
Sorimachi, Keiichi,Terada, Masahiro
supporting information; experimental part, p. 14452 - 14453 (2009/02/08)
A one-pot tandem isomerization/carbon-carbon bond forming sequence catalyzed by a ruthenium complex/Bronsted acid binary system is demonstrated. The method enables the use of readily available allylamides to deliver reactive imines under relay catalysis using a binary catalytic system. Subsequent Bronsted acid catalyzed carbon-carbon bond forming reactions of the generated imines with nucleophilic components afforded Friedel-Crafts and Mannich products in good yields. Copyright
N-amidation by copper-mediated cross-coupling of organostannanes or boronic acids with O-acetyl hydroxamic acids
Zhang, Zhihui,Yu, Ying,Liebeskind, Lanny S.
supporting information; experimental part, p. 3005 - 3008 (2009/04/18)
(Chemical Equation Presented) A general nonoxidative N-amidation of organostannanes and boronic acids has been developed. Under nonbasic conditions a wide variety of aryl, alkenyl, and heteroaryl organostannanes and boronic acids couple efficiently with O-acetyl hydroxamic acids in the presence of Cu(I) sources.
Total synthesis of TMC-95A and -B via a new reaction leading to Z-enamides. Some preliminary findings as to SAR
Lin, Songnian,Yang, Zhi-Qiang,Kwok, Benjamin H. B.,Koldobskiy, Michael,Crews, Craig M.,Danishefsky, Samuel J.
, p. 6347 - 6355 (2007/10/03)
A full account of the total syntheses of proteasome inhibitors TMC-95A and -B is provided. A key feature of the syntheses involved installation of a cis-propenylamide moiety by a thermal rearrangement of an α-silylallyl amide. The scope and mechanism of the enamide-forming reaction are discussed. Also provided are some preliminary results from SAR studies. It was found that simplified analogues can retain the full potency of proteasome inhibition.
