256382-53-3Relevant academic research and scientific papers
(4R)-3-Allenyl-4-(diphenylmethyl)-oxazolidin-2-one, an unsubstituted allenamide
Tracey, Michael R.,Grebe, Tyler P.,Brennessel, William W.,Hsung, Richard P.
, p. o830-o832 (2007/10/03)
The first X-ray structure of an unsubstituted allenamide, C 19H17NO2, is reported. The solid-state phase supports the notion that a key minimum conformation of allenamides can be invoked to rationalize the observed stereochemical outcomes in many of our methodological studies employing allenamides. This minimum conformation involves two important factors, i.e. having approximate coplanarity between the planes of the oxazolidinone ring and the internal olefin, and having the allene moiety facing away from the carbamate carbonyl group. The C-N-C=C torsion angle that quantifies this approximate coplanarity between the plane of the oxazolidinone ring and that of the internal olefin, as determined from this crystallographic study, is -19.1 (2)°. A minimized structural calculation, which determined this angle to be -16.1°, is in close agreement. Additional structural features include a probable π-π interaction between the allene moiety and a benzene ring, and non-classical hydrogen bonding in the form of weak C-H...O interactions that are responsible for the formation of two-dimensional networks.
Efficient preparations of novel ynamides and allenamides
Wei, Lin-Li,Mulder, Jason A.,Xiong, Hui,Zificsak, Craig A.,Douglas, Christopher J.,Hsung, Richard P.
, p. 459 - 466 (2007/10/03)
Practical syntheses of a series of novel ynamides and allenamides are described here. While a base-induced isomerization protocol of propargyl amides leads to an array of chiral and achiral allenamides, ynamides are prepared from enamides via bromination followed by base-induced elimination of the Z-bromoenamides. These ynamides and allenamides possess improved thermal stability compared to ynamines and allenamines. They can be isolated, purified, and handled with ease, and thus, should be synthetically more useful than traditional ynamines and allenamines.
First stereoselective inverse demand [4 + 2] cycloaddition reactions of novel chiral allenamides with heterodienes. Preparation of highly functionalized 2-arylpyranyl heterocycles
Wei, Lin-Li,Hsung, Richard P.,Xiong, Hui,Mulder, Jason A.,Nkansah, Nancy T.
, p. 2145 - 2148 (2008/02/09)
matrix presented The first stereoselective inverse demand [4 + 2] cycloaddition reactions of chiral allenamides with heterodienes are described here. These reactions lead to stereoselective synthesis of highly functionalized pyranyl heterocycles. A mechan
