303176-50-3Relevant academic research and scientific papers
Multiple component reactions: An efficient nickel-catalyzed Reformatsky-type reaction and its application in the parallel synthesis of β-amino carbonyl libraries
Adrian Jr., James C.,Snapper, Marc L.
, p. 2143 - 2150 (2003)
Multiple-component condensations (MCC) where three or more reactants combine to afford a new core structure possessing the molecular features of its composite building blocks is a powerful method for the preparation of molecular diversity. We have developed an efficient, nickel-catalyzed, Reformatsky-type three-component condensation (3CC) reaction that affords β-amino carbonyl compounds. The scope of the reaction is demonstrated both in the gram and microscale settings; 15 β-amino esters, amides, and a ketone were prepared efficiently at the mmol scale, and a library of 64 β-amino carbonyl compounds was generated at the μmol scale.
A new Yb3+-catalyzed pinacol and imine-coupling reaction
Aspinall, Helen C.,Greeves, Nicholas,Hin, Shane Lo Fan
experimental part, p. 1558 - 1561 (2010/06/13)
Ytterbium triflate, Yb(OTf)3, catalyzes the intermolecular reductive homocouplings of imines, aldehydes, and ketones at loadings of 5 mol % in the presence of Mg and Me3SiCl to give isolated yields of up to 95%. Diastereoselectivity of up to 4/96 (dl/meso) is achieved for aromatic aldehydes, up to 100% dl for aliphatic aldehydes, and 100% dl for an intramolecular imine coupling.
The first aza Diels-Alder reaction involving an α,β-unsaturated hydrazone as the dienophile: Stereoselective synthesis of C-4 functionalized 1,2,3,4-tetrahydroquinolines containing a quaternary stereocenter
Sridharan, Vellaisamy,Perumal, Paramasivan T.,Avendano, Carmen,Menendez, J. Carlos
, p. 1351 - 1353 (2008/01/01)
The reaction between aromatic imines and methacrolein dimethylhydrazone in the presence of 10% indium trichloride affords in good to excellent yields biologically and synthetically relevant 1,2,3,4-tetrahydroquinolines bearing a hydrazone function at C-4 in a one-pot process that involves the formation of two C-C bonds and the stereoselective generation of two stereocenters, one of them quaternary, and this constitutes the first example of an α,β-unsaturated dimethylhydrazone behaving as a dienophile in a hetero Diels-Alder reaction and the first vinylogous aza-Povarov reaction. This journal is The Royal Society of Chemistry.
