Steric course of the rhodium-catalyzed decarbonylation of chiral 4-methyl-[1-3H,2-2H1]pentanal.
(R)- and (S)-4-methyl-[1-3H,2-2H1]pentanal were prepared from L- and D-leucine via leucic acid and (S)- and (R)-4-methyl-[2-2H1]pentanoic acid. Decarbonylation of these samples with tris-(triphenylphosphine)rhodium chloride followed by Kuhn-Roth oxidation of the resulting 2-methylbutane gave chiral acetic acid of 35% e.e. S and 31% e.e. R configuration, respectively. The decarbonylation reaction thus proceeds with net retention of configuration, possibly accompanied by some racemization.
D002208:Caproates; D055598:Chemical Phenomena; D002621:Chemistry; D003903:Deuterium; D007930:Leucine; D012238:Rhodium; D013237:Stereoisomerism; D014316:Tritium
D002208:Caproates; D014316:Tritium; C018575:isocaproaldehyde; D003903:Deuterium; D012238:Rhodium; D007930:Leucine