393536-17-9Relevant articles and documents
Correction to: Nickel-catalyzed enantioselective reductive cross-coupling of styrenyl aziridines (Journal of the American Chemical Society (2017) 139 (5688-5691) DOI: 10.1021/jacs.7b03448)
Woods, Brian P.,Orlandi, Manuel,Huang, Chung-Yang Dennis,Sigman, Matthew S.,Doyle, Abigail G.
supporting information, p. 7744 - 7745 (2018/06/26)
Table of Contents. The enantiomer of the BiOx ligand that delivers the indicated absolute configuration of product is (R,R)-(4-heptyl)BiOx. The corrected graphic is shown below: Page 5690. The absolute configuration of ligand L7 (4-heptyl- BiOx) was misas
Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics
Wünsch, Matthias,Schr?der, David,Fr?hr, Tanja,Teichmann, Lisa,Hedwig, Sebastian,Janson, Nils,Belu, Clara,Simon, Jasmin,Heidemeyer, Shari,Holtkamp, Philipp,Rudlof, Jens,Klemme, Lennard,Hinzmann, Alessa,Neumann, Beate,Stammler, Hans-Georg,Sewald, Norbert
supporting information, p. 2428 - 2441 (2017/12/06)
The amide moiety of peptides can be replaced for example by a triazole moiety, which is considered to be bioisosteric. Therefore, the carbonyl moiety of an amino acid has to be replaced by an alkyne in order to provide a precursor of such peptidomimetics. As most amino acids have a chiral center at Cα, such amide bond surrogates need a chiral moiety. Here the asymmetric synthesis of a set of 24 N-sulfinyl propargylamines is presented. The condensation of various aldehydes with Ellman's chiral sulfinamide provides chiral N-sulfinylimines, which were reacted with (trimethylsilyl)ethynyllithium to afford diastereomerically pure N-sulfinyl propargylamines. Diverse functional groups present in the propargylic position resemble the side chain present at the Cα of amino acids. Whereas propargylamines with (cyclo)alkyl substituents can be prepared in a direct manner, residues with polar functional groups require suitable protective groups. The presence of particular functional groups in the side chain in some cases leads to remarkable side reactions of the alkyne moiety. Thus, electron-withdrawing substituents in the Cα-position facilitate a base induced rearrangement to α,β-unsaturated imines, while azide-substituted propargylamines form triazoles under surprisingly mild conditions. A panel of propargylamines bearing fluoro or chloro substituents, polar functional groups, or basic and acidic functional groups is accessible for the use as precursors of peptidomimetics.
Further studies toward the stereocontrolled synthesis of silicon-containing peptide mimics
Hernandez, Dacil,Lindsay, Karl B.,Nielsen, Lone,Mittag, Tina,Bjerglund, Klaus,Friis, Stig,Mose, Rasmus,Skrydstrup, Troels
supporting information; experimental part, p. 3283 - 3293 (2010/08/07)
Further studies are reported on the utilization of the versatile reaction between chiral sulfinimines and alkyldiphenylsilyl lithium reagents with the goal of preparing a wide range of silanediol-based protease inhibitors. In particular, focus has been placed to demonstrate how a number of genetically encoded amino acid side chains such as serine, threonine, tyrosine, lysine, proline, arginine, aspartate and asparagine might be incorporated into the overall approach. Efforts to apply this synthetic methodology for accessing biologically relevant silanediol dipeptide mimics are also described. This includes the synthesis of a potential inhibitor of the human neutrophil elastase, as well as a diphenylsilane mimic of a hexapeptide fragment of the human islet amyloid polypeptide.
