216753-82-1Relevant articles and documents
Novel thiol- and thioether-containing amino acids: Cystathionine and homocysteine families
Longobardo, Luigi,Cecere, Nunzia,DellaGreca, Marina,De Paola, Ivan
, p. 443 - 448 (2013/07/27)
Natural l-homocysteine and l,l-cystathionine, along with a series of unnatural analogues, have been prepared from l-aspartic and l-glutamic acid. Manipulation of the protected derivatives provided ω-iodoamino acids, which were used in thioalkylation react
Concise Synthesis of Enantiomerically Pure Phenylalanine, Homophenylalanine, and Bishomophenylalanine Derivatives Using Organozinc Chemistry: NMR Studies of Amino Acid-Derived Organozinc Reagents
Jackson, Richard F. W.,Moore, Rebecca J.,Dexter, Charles S.,Elliott, Jason,Mowbray, Charles E.
, p. 7875 - 7884 (2007/10/03)
Protected phenylalanines 23 (seven examples), homophenylalanines 7 (eight examples), and bishomophenylalanines 8 (seven examples) have been prepared by palladium-catalyzed coupling of the amino acid-derived organozinc reagents 13, 5, and 6, respectively, with aryl iodides. While the reactions of the zinc reagent 13 may be conducted in both THF and DMF as solvent, the results obtained in DMF are generally superior. In the case of the reagents 5 and 6 the results are far superior in DMF. NMR investigations on the structure of the zinc reagents 13 in THF suggest that there is strong intramolecular coordination of the urethane carbonyl group, whereas in DMF this interaction is completely suppressed.
