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Lyle, R. E., Nelson, D. A. and Anderson, P. S. Tetrahedron Lett. (1962) 553; Anderson, P. S. and Lyle, R. E. (1964) 153
With respect to organic synthesis, this catalytic system is compatible with a broad range of functional groups. Indeed, alkenes containing electron-donating (triethylsilyl 1m) as well as electron-withdrawing substituents (perfluoroalkyl 1n, phthalimido 1o) in direct conjugation with the olefin led to functionalized esters in very good yield and regioselectivity. Notably, also methyl 2-acetamidoacrylate—an example of a notoriously unreactive push-pull olefin—produced the amino acid derivative 2p in 88% yield and highly selectively. Other olefins with remote substituents, for example, hydroxyl, nitrile, chloride and ester groups, underwent methoxycarbonylation smoothly and afforded the desired products 2q- t in 65–96% yields, although in some cases the regioselectivity was lower. As an example for the carbonylation of renewable olefins (terpenes), we tested limonene. In contrast to known carbonylation catalysts 40, 41 double methoxycarbonylation occurred preferentially to deliver the diester product 2u in high yield. Methoxycarbonylation of pharmaceuticals Lowman, V. C., quoted in Heterocyclic Compounds, ed. Elderfield, R. C., Vol. 4, p. 243, New York (Wiley) 1952 Knifton, J. F. Linear carboxylic acid esters from.alpha. olefins. 2. Catalysis by homogeneous palladium complexes. J. Org. Chem. 41, 2885–2890 (1976). b) Koenigs, E., Gerdes, H. C. and Sirot, A. Ber. dtsch. chem. Ges. 61 (1928) 1022; ( c) Maier-Bode, H. 69 (1936) 1534; den Hertog, H. J., van der Plas, H. C. and Buurman, D. J. Recl Trav. chim. Pays-Bas Belg. 77 (1958) 963
Reference
Helferich, B. with Moog, L. and Jünger, A. 58 (1925) 872; with Sieber, H. 59 (1926) 600; Rebek, M. 62 (1929) 2508; with Kramaršic, V. ibid. All The ultimate goal for any new catalyst is to be superior compared with known systems in ‘real life’ applications in industry. As mentioned vide supra, the methoxycarbonylation of ethylene constitutes a key step in the Lucite α-process for the preparation of methyl methacrylate.
In this work, the latest improved version of the genomic assembly [ 18] allowed us to fill the gap in our knowledge [ 5] regarding the genomic organisation of the dromedary TRA/TRD locus, which represents the most complex among the TR loci.a) Pieterse, H. J. and den Hertog, H. J. Recl Trav. chim. Pays-Bas Belg. 81 (1962) 855; ( b) Martens, R. J., den Hertog, H. J. and van Ammers, M. Tetrahedron Lett. (1964) 3207; a) Ashida, T., Hirokawa, S. and Okaya, Y. Acta crystallogr. 18 (1965) 122; ( b) Laurent, A. ibid. 799