1593585-84-2Relevant articles and documents
Enantioselective ruthenium-catalyzed 1,3-dipolar cycloadditions between C -carboalkoxy ketonitrones and methacrolein: Solvent effect on reaction selectivity and its rational
Selim, Khalid B.,Martel, Arnaud,Laurent, Mathieu Y.,Lhoste, Jér?me,Py, Sandrine,Dujardin, Gilles
, p. 3414 - 3426 (2014/05/06)
A catalytic 1,3-dipolar cycloaddition between carboalkoxy ketonitrones and methacrolein under the effect of chiral ruthenium Lewis acid (R,R-1) was developed with high regio-, diastereo-, and enantiocontrol. The diastereochemical outcome of the cycloaddition reaction is marked by a significant solvent effect, and a divergent endo or exo control can be tuned by an appropriate choice of both the solvent and the N- and O-substituents of the ketonitrone. A rationale of the solvent effect, based on the computational study of the interactions between the methacrolein-Ru complex and its counteranion (SbF6-), is proposed to explain the selectivities obtained.