64889-55-0Relevant articles and documents
Taking control of P1, P1′ and double bond stereochemistry in the synthesis of Phe-Phe (E)-alkene amide isostere dipeptidomimetics
Wiktelius, Daniel,Luthman, Kristina
, p. 603 - 605 (2007)
A protocol for the stereocontrolled independent preparation of Phe-Phe trans-vinyl amide isostere dipeptideomimetics was developed based on a Wittig-type reaction. In the reaction two chiral building blocks were joined with excellent E-selectivity to give
Asymmetric hydroformylation of Z -Enamides and enol esters with rhodium-bisdiazaphos catalysts
Abrams, M. Leigh,Foarta, Floriana,Landis, Clark R.
supporting information, p. 14583 - 14588 (2015/01/08)
Asymmetric hydroformylation (AHF) of Z-enamides and Z-enol esters provides chiral, alpha-functionalized aldehydes with high selectivity and atom economy. Rh-bisdiazaphospholane catalysts enable hydroformylation of these challenging disubstituted substrates under mild reaction conditions and low catalyst loadings. The synthesis of a protected analog of l-DOPA demonstrates the utility of AHF for enantioselective, atom-efficient synthesis of peptide precursors.
A facile one-pot synthesis of 2-fluoroalkyl 1,3-imidazolines and 1,3-oxazolines through imidoyl halide intermediates
Jiang, Haizhen,Sun, Lan,Yuan, Shijie,Lu, Wenjun,Wan, Wen,Zhu, Shizheng,Hao, Jian
supporting information; experimental part, p. 2858 - 2863 (2012/05/05)
A facile one-pot procedure has been developed for the synthesis of 1,3-imidazolines and 1,3-oxazolines bearing fluorinated alkyl groups at the 2-position. The reaction involves the condensation of N-monosubstituted ethane-1,2-diamines or 2-aminoethanols with a fluorinated carboxylic acid in the presence of PPh3/CX4. The proposed mechanism is that the amide intermediates were initially formed, and then converted to the imidoyl halide intermediates in the presence of PPh3/CX4, followed by rapid intramolecular cyclization to 1,3-diazoline products. This protocol allows for the synthesis of 2-bromodifluoromethyl-1,3-imidazoline, a useful CF2Br-heterocyclic building block, which can be used for the synthesis of gem-difluoromethylene linked compounds.