119973-55-6Relevant articles and documents
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
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.
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.
Axially chiral dicarboxylic acid catalyzed activation of quinone imine ketals: Enantioselective arylation of enecarbamates
Hashimoto, Takuya,Nakatsu, Hiroki,Takiguchi, Yuka,Maruoka, Keiji
supporting information, p. 16010 - 16013 (2013/11/19)
The synthetic utility of quinone imine ketals in the context of asymmetric catalysis was disclosed for the first time. By expanding the utility of chiral Bronsted acid catalysis to the electrophilic activation of quinone imine ketals, we succeeded in the development of highly enantioselective arylation of encarbamates to give α-amino-β-aryl ethers wherein quinone imine ketals act as functionalized aromatic ring surrogate. Further transformations of the products were also examined to establish procedures to provide chiral β-aryl amines and α-aryl esters.
Easy access to enamides: A mild nickel-catalysed alkene isomerization of allylamides
Wang, Lu,Liu, Chao,Bai, Ruopeng,Pan, Yani,Lei, Aiwen
supporting information, p. 7923 - 7925 (2013/09/02)
The first Ni-catalysed alkene isomerization of allylamides for the synthesis of enamides was demonstrated. Various substituted N-allylamides were found to be suitable substrates for this isomerization. Isotopic labelling experiments showed that it is an i
Regioselective Rh(I)-catalyzed sequential hydrosilylation toward the assembly of silicon-based peptidomimetic analogues
Min, Geanna K.,Skrydstrup, Troels
experimental part, p. 5894 - 5906 (2012/09/21)
A highly regioselective Rh(I)-catalyzed hydrosilylation of enamides is presented. This mild protocol allows access to a wide variety of different arylsilanes with substitution at the β-position of the enamide and functionalization on the alkyl chain tethered to the silane. This protocol is extended to include a sequential one-pot hydrosilylation. Using diphenylsilane as the appendage point, hydrosilylation of a protected allyl alcohol followed by hydrosilylation of an enamide generates a complex organosilane in one step. This highly convergent strategy to synthesize these functionalized systems now provides a way for the rapid assembly of a diverse collection of silane-based peptidomimetic analogues.
Synthesis and Reactivity of β-Lactones Derived from L-Threonine and Related Amino Acids
Pansare, Sunil V.,Vederas, John C.
, p. 2311 - 2316 (2007/10/02)
The synthesis and nucleophilic ring opening of optically pure N-protected α-amino-β-alkyl β-lactones was investigated.Treatment of N-BOC-L-threonine (8) and N-BOC-L-allo-threonine (9) under modified Mitsunobu conditions (Ph3P, dimethyl azodicarboxylate, -
