5470-13-3Relevant academic research and scientific papers
A chiral spiroborate anion from diphenyl-l-tartramide [B{l-Tar(NHPh)2}2]- applied to some challenging resolutions
Wong, Lawrence W.-Y.,Tam, Gemma S.-S.,Chen, Xiaoyan,So, Frederick T.-K.,Soecipto, Aristyo,Sheong, Fu Kit,Sung, Herman H.-Y.,Lin, Zhenyang,Williams, Ian D.
, p. 4831 - 4848 (2018)
The chiral spiroborate anion [B{l-Tar(NHPh)2}2]- has been prepared as simple salts K, NH4, Na in high yield and purity. Its structural features have been examined by single crystal XRD and DFT calculations and indicate that conformational arrangements are dominated by intramolecular NH - -OC inter-amide hydrogen bonds. These confer predictable shape, as well as a clear binding site for ion-pair formation. The potential of this anion for resolution by diastereomeric salt formation was then tested using five challenging racemic amines of type NH2CHR1R2 with high shape similarity between their enantiomers. Organo-ammonium salts from these were made directly from a simple 1-pot reaction from racemic amine, boric acid and 2 eq. N,N′-diphenyl-l-tartramide in MeOH. The products are single phase crystalline solids with moderate to excellent enantioexcesses up to 95% ee. They show conserved NH3R+ binding and layered packing arrangements, all with short 5.5 ? axes. Based on chiral HPLC the initial [B{l-Tar(NHPh)2}2] salt from rac-phenylglycinol has [S-NH3CH(CH2OH)Ph]+ with 95% ee and the salt from rac-1-phenylpropylamine is also well resolved (>91% ee) in a single step. Three disorder modes that limit resolution in the other salts were identified at the cation site-H/R1 site exchange, R1/R2 site exchange or C-H re-pyramidalization. Extension to a family of such aryltartramide anions may allow crystal engineering of the cation binding pockets to overcome the disorder inherent to such resolutions.
Supramolecular chirality in organo-, hydro-, and metallogels derived from bis-amides of L -(+)-tartaric acid: Formation of highly aligned 1D silica fibers and evidence of 5-c net SnS topology in a metallogel network
Das, Uttam Kumar,Dastidar, Parthasarathi
supporting information, p. 13079 - 13090 (2013/01/15)
A series of bis-amides derived from L-(+)-tartaric acid was synthesized as potential low-molecular-weight gelators. Out of 14 bis-amides synthesized, 13 displayed organo-, hydro-, and ambidextrous gelation behavior. The gels were characterized by methods
Diamines having a C2 symmetry. Synthesis and application as ligands in the hydrogenation of prochiral substrates over rhodium complexes
Shainyan,Ustinov,Bel'skii,Nindakova
, p. 104 - 110 (2007/10/03)
Chiral diamines having a C2 symmetry, (4S,5S)-2,2-dimethyl-4,5-bis(aminomethyl)-1,3-dioxolane and (5S,5′ S)-2,2,2′,2′-tetramethyl-3,3′-diphenyl-5,5′ -bioxazolidine, were synthesized on the basis of (+)-(2R,3R)-tartaric acid. Their structure was proved by X-ray analysis. The products were used as ligands in rhodium catalyst for enantioselective hydrogenation of α -acetamidocinnamic and itaconic acids.
Solvent-free synthesis of tartramides under microwave activation
Massicot,Plantier-Royon,Portella,Saleur,Sudha
, p. 2441 - 2444 (2007/10/03)
The preparation of aliphatic, aromatic or functionalized tartramides directly from tartaric acid and amines under microwave activation is described. The inexpensive, solvent free and fast reaction conditions are the important features of the procedure.
NEW FACILE SYNTHESIS OF α-HYDROXYAMIDES:INTERMOLECULAR AND INTRAMOLECULAR CATALYSIS IN THE REACTION OF α-HYDROXYCARBOXYLIC ACIDS WITH N-SULFINYLAMINES.
Shin, Jai Moo,Kim, Yong Hae
, p. 1921 - 1924 (2007/10/02)
α-Hydroxycarboxylic acids (1) reacted with N-sulfinylanilines (2) to give the corresponding α-hydroxyanilides (5) in quantitative yields under mild condition: the reaction appears to involve intermolecular catalysis by the carboxylic acid moiety and intra
