1082935-54-3Relevant articles and documents
Product Selectivity in KAHA Ligations: Ester vsAmide Formation with Cyclic Hydroxylamines
Rohrbacher, Florian,Baldauf, Simon,Wucherpfennig, Thomas G.,Bode, Jeffrey W.
supporting information, p. 1929 - 1933 (2017/09/13)
Cyclic hydroxylamines form esters instead of the expected amides as major product upon reaction with α-ketoacids. In this report, we document a systematic investigation into the effect of the hydroxylamine structure and the solvent mixture on the product
Amidation of esters with amino alcohols using organobase catalysis
Caldwell, Nicola,Campbell, Peter S.,Jamieson, Craig,Potjewyd, Frances,Simpson, Iain,Watson, Allan J. B.
, p. 9347 - 9354 (2014/12/11)
A catalytic protocol for the base-mediated amidation of unactivated esters with amino alcohol derivatives is reported. Investigations into mechanistic aspects of the process indicate that the reaction involves an initial transesterification, followed by an intramolecular rearrangement. The reaction is highly general in nature and can be extended to include the synthesis of oxazolidinone systems through use of dimethyl carbonate.
Umpolung reactivity in amide and peptide synthesis
Shen, Bo,Makley, Dawn M.,Johnston, Jeffrey N.
experimental part, p. 1027 - 1032 (2011/08/06)
The amide bond is one of natureg€s most common functional and structural elements, as the backbones of all natural peptides and proteins are composed of amide bonds. Amides are also present in many therapeutic small molecules. The construction of amide bonds using available methods relies principally on dehydrative approaches, although oxidative and radical-based methods are representative alternatives. In nearly every example, carbon and nitrogen bear electrophilic and nucleophilic character, respectively, during the carbong€"nitrogen bond-forming step. Here we show that activation of amines and nitroalkanes with an electrophilic iodine source can lead directly to amide products. Preliminary observations support a mechanism in which the polarities of the two reactants are reversed (German, umpolung) during carbong€"nitrogen bond formation relative to traditional approaches. The use of nitroalkanes as acyl anion equivalents provides a conceptually innovative approach to amide and peptide synthesis, and one that might ultimately provide for efficient peptide synthesis that is fully reliant on enantioselective methods.
