103067-78-3Relevant articles and documents
Large scale enantiomeric synthesis, purification, and characterization of ω-unsaturated amino acids via a Gly-Ni(II)-BPB-complex
Gu, Xuyuan,Ndungu, John M.,Qiu, Wei,Ying, Jinfa,Carducci, Michael D.,Wooden, Hank,Hruby, Victor J.
, p. 8233 - 8243 (2007/10/03)
The enantiomeric syntheses of ω-unsaturated amino acids and β-substituted ω-unsaturated amino acids were accomplished by using Gly-Ni-2[N-(N′-benzylprolyl)amino]benzophenone (BPB) as a chiral auxiliary. The synthesis provides excellent yields and high diastereoselectivities. The product crystallization followed by isomer epimerization strategy makes the reaction practical and useful for large-scale preparations. Dialkylation of the Ni(II)-complex, which was designed for mechanistic considerations, revealed that high diastereoselectivity is obtained due to the thermodynamic conformational stability of the Ni(II)-complex. The assignment of absolute configuration was accomplished by NMR, which is supported by corresponding X-ray structure and optical rotation data. Both enantiomerically pure amino acids can be synthesized in this alkylation-hydrolysis two-step strategy in multi gram scales.
Ruthenium-catalyzed ring closing olefin metathesis of non-natural α-amino acids
Rutjes, Floris P. J. T.,Schoemaker, Hans E.
, p. 677 - 680 (2007/10/03)
The use of various enantiopure amino acid-derived diolefins as substrates for the ring closing olefin metathesis reaction (RCM) has been investigated. This reaction has been shown to be an efficient transformation for providing highly functionalized 6- and 7-membered ring amino acids.