160167-60-2Relevant academic research and scientific papers
Conformational study and enantioselective, regiospecific syntheses of novel aminoxy trans-proline analogues derived from an acylnitroso Diels-Alder cycloaddition
Shireman,Miller,Jonas,Wiest
, p. 6046 - 6056 (2007/10/03)
The cis/trans isomerization of the proline amide bond has many implications in biological processes. The conformations of representative acylnitroso-derived proline analogues derived from cyclopentadiene were shown to exist exclusively as the E or trans conformation in CD2Cl2. The energetically favored conformations were determined using COSMO self-consistent reaction field calculations at the B3LYP/6-31G* level of theory in addition to low temperature 1H NMR studies. The syntheses of the acylnitroso-derived peptides utilized two methods to selectively functionalize either of two chemically similar esters in the acylnitroso-derived amino acids. A novel transpeptidation of the amino acid that controlled the absolute stereochemistry in the acylnitroso Diels-Alder cycloaddition took advantage of an activated aminoxy amide linkage to control regiochemistry. Alternatively, an enantioselective and regiospecific enzymatic resolution of a racemic dimethyl ester provided a novel aminoxy acid.
Amino Acid-Derived Chiral Acyl Nitroso Compounds: Diastereoselectivity in Intermolecular Hetero Diels-Alder Reactions
Ritter, Allen R.,Miller, Marvin J.
, p. 4602 - 4611 (2007/10/02)
The diastereoselectivities of chiral acyl nitroso dienophiles derived from optically pure N-protected α-amino hydroxamic acids have been determined in intermolecular hetero Diels-Alder reactions.The cycloaddition reactions afforded synthetically useful qu
