23519-90-6Relevant articles and documents
Amino acid-bearing ROMP polymers with a stereoregular backbone
Lee, Jae Chul,Parker, Kathlyn A.,Sampson, Nicole S.
, p. 4578 - 4579 (2006)
The ruthenium-catalyzed ring-opening polymerization (ROMP) of 1-cyclobutenecarbonyl glycine methyl ester provides translationally invariant, head-to-tail ordered polymers. This polybutadiene backbone contains (within the limits of detection) only E-trisub
Silyl Radical-Mediated Activation of Sulfamoyl Chlorides Enables Direct Access to Aliphatic Sulfonamides from Alkenes
Gouverneur, Véronique,Hell, Sandrine M.,Laudadio, Gabriele,Meyer, Claudio F.,Misale, Antonio,No?l, Timothy,Trabanco, Andrés A.,Willis, Michael C.
supporting information, p. 720 - 725 (2020/02/20)
Single electron reduction is more challenging for sulfamoyl chlorides than sulfonyl chlorides. However, sulfamoyl and sulfonyl chlorides can be easily activated by Cl-atom abstraction by a silyl radical with similar rates. This latter mode of activation was therefore selected to access aliphatic sulfonamides, applying a single-step hydrosulfamoylation using inexpensive olefins, tris(trimethylsilyl)silane, and photocatalyst Eosin Y. This late-stage functionalization protocol generates molecules as complex as sulfonamide-containing cyclobutyl-spirooxindoles for direct use in medicinal chemistry.
Synthesis of chiral cyclobutanes via rhodium/diene-catalyzed asymmetric 1,4-addition: A dramatic ligand effect on the diastereoselectivity
Chen, Ya-Jing,Hu, Tian-Jiao,Feng, Chen-Guo,Lin, Guo-Qiang
supporting information, p. 8773 - 8776 (2015/05/20)
A highly diastereo- and enantioselective rhodium-catalyzed arylation of cyclobutenes for the efficient synthesis of chiral cyclobutanes has been developed. Chiral diene ligands exhibited excellent capability for the reaction diastereoselectivity control.
Synthesis of the 1-monoester of 2-ketoalkanedioic acids, for example, octyl α-ketoglutarate
Jung, Michael E.,Deng, Gang
, p. 11002 - 11005 (2013/02/22)
Oxidative cleavage of cycloalkene-1-carboxylates, made from the corresponding carboxylic acids, and subsequent oxidation of the resulting ketoaldehyde afforded the important 1-monoesters of 2-ketoalkanedioic acids. Thus ozonolysis of octyl cyclobutene-1-carboxylate followed by sodium chlorite oxidation afforded the 1-monooctyl 2-ketoglutarate. This is a cell-permeable prodrug form of α-ketoglutarate, an important intermediate in the tricarboxylic acid (TCA, Krebs) cycle and a promising therapeutic agent in its own right.
