Trogerization

Troger and Schwarzenberg have isolated a base (m.p. 53°, b.p. 225-30° picrate, m.p. 237° (dec.) ) isomeric with tropine and 4-tropinc, from coca leaves. 

From a spurious angostura bark, Troger isolated an unnamed alkaloid, ( jjHjgOjNj, m.p. 167°, soluble in alkali or acid and giving a a ystallinc perchlorate and methiodide. 

The hydrogenation of ehtyl pyurvate (EtPy) was carried out at 23 °C in a SS autoclave equipped with an injection chamber for separate introduction of the modifier Cinchonidine (CD) and Troger s base (TB) was used as modifiers. Different batches of EtPy, (Fluka) and Pt/Al203 catalysts (Engelhard E 4759, 5 %w Pt, Dpt = 25 %) were used. Experimental details incliding GC analysis can be found elsewhere [3,12]. The optical yield was calculated as e.e. = ([R]-[S])/([R]+[S]). The e.e. values were corrected for the amount of racemic product formed in minor amount in the reactor prior to the injection of CD. 

Monte-Carlo simulation method was used to investigate the interaction of the [CDdosed-MePy] complexes with Pt (111) surface. The result shown in Figure 5 indicates that the shielded complex can maintain its entity even after adsorption. Further computer modeling indicated that there are other molecules with the ability to induce SE. In this respect Troger s bases are of particular interest. The calculated Troger s base-methyl pyruvate complex (R form) is shown in Figure 6. 

Figure 6, Troger s base-methyl pyruvate complex.

Table 1. Hydrogenation of ethyl puruvate in the presence of Troger s base...

Complexes (65) and (66) result from the reaction of IrCl3 with inah and PPh3 (inah = isonicotinic acid hydrazide).92 Reaction of Troger s base (tb) (67) with IrCl3 yields dark violet tb 2IrCl3 (6S).93 (68) was not catalytically active towards the hydrosilylation of alkynes. 

A similar reaction of thiophene analogues of Troger s base with formaldehyde was carried out by Kobayashi et al. <2002J (P1)1963>. 

Figure 3.12 Enantioseparation of TrOger s base on (a) microcrystalline cellulose triacetate (CTA I) and (b) 21 coated on silica gel. Column, 25 x 0.46 (i.d.) cm eluent ethanol-HoO (7/3) flow rate, 0.5 ml/min).

Figure 16.17 Amine-terminated polypropylene imine) dendrimers act as tridentate ligands for the complexation of transition metals [217] (a), and can function as templates for the assembly of Troger s base dizinc(ll) bis-porphyrin molecules, (b) [218]...

Herold C, Heinz R, Radespiel-Troger M, Schneider HT, Schuppan D,Hahn EG (2001) Liver... 

Kaupp G (2004) Troger s base derivatives. In Encyclopedia of supramolecular chemistry. Marcel Dekker, New York, pp 1516-1524... 

Zernig G, Troger J, Saria A (1993) Different behavioral profiles of the non-peptide substance P (NKl) antagonists CP-96,345 and RP 67580 in Swiss albino mice in the black- and-white box. Nemosci Lett 151 64-66... 

Troger s base, the resolution of which with a strongly acidic resolving agent is accompanied by a crystallization-induced asymmetric transformation (also see p426)87. 

Acids and bases. These can be converted to various salts. For example, the absolute configuration of dimethyl (M)-5,6,8,10-tetramethyl-l,2-heptalenedicarboxylate (p 404) was determined by X-ray analysis of its (+)-ephedrine salt84, and the absolute configuration of Troger s base (p 404) by X-ray analysis of a salt with an acid of known configuration87. 

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