88425-24-5Relevant articles and documents
Chiral phosphoric acid catalyzed enantioselective annulation of acyclic enecarbamates to: In situ -generated ortho -quinone methides
Gharui, Chandan,Singh, Shreya,Pan, Subhas Chandra
supporting information, p. 7272 - 7276 (2017/09/25)
The first organocatalytic asymmetric reaction of acyclic enecarbamates with o-quinone methides is disclosed. BINOL-based phosphoric acid catalysts were found to be suitable for the annulation reaction. With 10 mol% of the TRIP catalyst, high yields as well as excellent diastereo- and enantioselectivities are achieved for a variety of 2,3,4-trisubstituted chroman products.
A synthetic approach to N -aryl carbamates via copper-catalyzed Chan-Lam coupling at room temperature
Moon, Soo-Yeon,Kim, U. Bin,Sung, Dan-Bi,Kim, Won-Suk
, p. 1856 - 1865 (2015/02/19)
A mild and efficient synthesis of N-arylcarbamates was achieved by reacting azidoformates with boronic acids in the presence of 10 mol % of copper chloride catalyst. The reaction proceeds readily in an open flask at room temperature without additional base, ligand, or additive. Rapid access to urea analogues via a two-step one-pot procedure is enabled by reacting N-arylcarbamates with aluminum-amine complexes. In addition, among several boronic acid derivatives prepared, dimethylphenyl boronate was found to react rapidly in its reaction with benzyl azidoformate, invoking in situ generation of this species in the catalytic cycle.
Decarbonylative approach to the synthesis of enamides from amino acids: Stereoselective synthesis of the (Z)-aminovinyl-d-cysteine unit of mersacidin
Garcia-Reynaga, Pablo,Carrillo, Angela K.,Vannieuwenhze, Michael S.
, p. 1030 - 1033 (2012/04/04)
The Pd- and Ni-promoted decarbonylation of amino acid thioesters proceeds smoothly to yield enamides. The synthesis of the (S)-(Z)-AviMeCys subunit of mersacidin, an MRSA-active lantibiotic, via this approach, is described.
Enamides accessed from aminothioesters via a Pd(0)-catalyzed decarbonylative/β-hydride elimination sequence
Min, Geanna K.,Hernandez, Dacil,Lindhardt, Anders T.,Skrydstrup, Troels
supporting information; experimental part, p. 4716 - 4719 (2010/12/25)
A facile synthesis of various enamides from aminothioesters via a palladium(0)-catalyzed decarbonylation/β-hydride elimination is reported. This protocol was applied to mercaptopyridyl C-terminal modified peptides for the generation of enamides without ep
Ambient temperature synthesis of high enantiopurity N-protected peptidyl ketones by peptidyl thiol ester-boronic acid cross-coupling
Yang, Hao,Li, Hao,Wittenberg, Ruediger,Egi, Masahiro,Huang, Wenwei,Liebeskind, Lanny S.
, p. 1132 - 1140 (2007/10/03)
α-Amino acid thiol esters derived from N-protected mono-, di-, and tripeptides couple with aryl, π-electron-rich heteroaryl, or alkenyl boronic acids in the presence of stoichiometric Cu(I) thiophene-2-carboxylate and catalytic Pd2(dba)3/triethylphosphite to generate the corresponding N-protected peptidyl ketones in good-to-excellent yields and in high enantiopurity. Triethylphosphite plays a key role as a supporting ligand by mitigating an undesired palladium-catalyzed decarbonylation-β-elimination of the α-amino thiol esters. The peptidyl ketone synthesis proceeds at room temperature under nonbasic conditions and demonstrates a high tolerance to functionality.
Preparation and allylation of enamides and enecarbamates generated via iron(0) reduction of oximes and derivatives
Sun, Cuixiang,Weinreb, Steven M.
, p. 3585 - 3588 (2008/03/14)
Reductive acylation of oximes and oxime carbonates can be effected with iron powder in the presence of an acid chloride or a chloroformate to produce enamides or enecarbamates. Georg Thieme Verlag Stuttgart.
Curtius rearrangement of aromatic carboxylic acids to access protected anilines and aromatic ureas
Lebel, Helene,Leogane, Olivier
, p. 5717 - 5720 (2007/10/03)
(Diagram presented) The reaction of a chloroformate or di-tert-butyl dicarbonate and sodium azide with an aromatic carboxylic acid produces the corresponding acyl azide, presumably through the formation of an azidoformate. The acyl azide undergoes a Curtius rearrangement to form an isocyanate derivative which is trapped either by an alkoxide or by an amine to form the aromatic carbamate or urea. The reaction conditions are compatible with a variety of functional groups and allow the synthesis of a number of aniline derivatives containing alkyl, halide, nitro, ketone, ether, and thioether substituents.
Retro-Inverso Isomerization of Peptides: Side Reactions in the Synthesis of N,N'-Diacyl-1,1-diamino-2-phenylethane Derivatives
Chorev, Michael,MacDonald, Scott A.,Goodman, Murray
, p. 821 - 827 (2007/10/02)
In general, the synthesis of retro-inverso peptides requires the formation of diacylated gem-diaminoalkyl structures.One way to prepare these gem-diaminoalkyl residues involves the Curtius rearrangement of the N-acylated amino acid hydrazides to the corre
