Table 3 Selective Pd-catalysed dicarbonylation for the synthesis of non-symmetrical malonamides with biologically relevant molecules

From: Synthesis of non-equivalent diamides and amido-esters via Pd-catalysed carbonylation

  1. Standard reaction conditions: 1 (0.2 mmol), 2 (0.3 mmol), 3 (0.3 mmol), Pd(MeCN)2Cl2 (2.5 mol%), L14 (10 mol%), CH2Cl2 (2.0 ml), CO (40 bar), 20 h at 60 °C. Isolated yields are given within parentheses. NMR spectroscopic yields (values before parentheses) and z:e-selectivities of 4 were determined by crude 1H NMR spectroscopic analysis using dibromomethane as the internal standard. Unless otherwise noted, the e:z ratio is >20:1 in all cases. a0.3 mmol amino acid ester hydrochloride and 0.3 mmol Et3N were used. bIsolated as mixture of diastereoisomers in an unknown ratio, the ratio could not be determined owing to overlapping signals in in the crude 1H NMR spectra. c11-(Piperazin-1-yl)dibenzo[b,f][1,4]thiazepine dihydrochloride and 0.6 mmol Et3N were used.
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