Pyrrolidides

Figure 17.4 (a) Compound 23 bound to DPP-4. The overlay of compound 23 (yellow) and the substrate analogue valine pyrrolidide (magenta) shows a similar orientation between the two compounds. Interactions of compound 23 with DPP-4 are shown as red dotted lines, (b) Compound 48 bound to DPP-4. Interactions of compound 48 with DPP-4 are shown as red dotted lines. 

Ashton, W.T., Dong, H., Sisco, R.M., Doss, G.A., Leiting, B., Patel, R.A., Wu, J.K., Marsilio, F., Thornberry, N.A. and Weber, A.E. (2004) Diastereoselective synthesis and configuration-dependent activity of (3-substituted-cycloalkyl) glycine pyrrolidides and fhiazolidides as dipeptidyl peptidase IV inhibitors. Bioorganic at Medicinal Chemistry Letters, 14, 859-863. 

Dimers with a 1,2-bismethylenecyclobutane structure were obtained from 585 [240], 590 [238], 591 [241], 592 [242], 593 [243] and from the pinene derivative 597 [244]. The interception of 592 by 1,3-diphenylisobenzofuran (DPIBF) afforded two diastereomeric [4+ 2]-cycloadducts [245], Bicyclo[5.1.0]octa-3,4-diene (594) was generated by /3-elimination and trapped by sodium pyrrolidide because of the question of the extent to which the corresponding bicyclooctyne is formed in addition to 594 [184], Liberated by /3-elimination from ll,ll-dichloro-l,6-methano[10]annulene in... 

The existence of such complexes has been confirmed by kinetic experiments, multidimensional and multinuclear ( Li, H) NMR, and the beneficial effect of substitutions at the lithium pyrrolidide ring outlined . Nevertheless, recent computational studies... 

Die diastereoselektive Alkylierung des Dianions von N-Benzoyl-glycin-[(S)-2-meth-oxymethyl-pyrrolidid] (IV R3 = H) bzw. -( —)-menthylester (V R3 = H) gelingt in Abhan-... 

Die Anwendung einer nur katalytischen Menge eines Lithium-amids (Lithium-pyrrolidid) ist fur die mit 90%iger Ausbeute verlaufende Reaktion von Benzophenon-methylimin mit Isopren zu 2,2-Diphenyl-3-isopropenyl-pyrrolidin beschrieben3. 

By heating the racemic Robinson annelation product (249) with an equimolar amount of (S)-proline pyrrolidide (250), the related dienamine (251) was obtained, which, upon hydrolysis was converted to (S)-(249)248). 

The pyrrolidide tetramer [(trneda)2(Li (CH2j,CH2j4l and hexamer [(pmdeta)2-I----------1... 

Dasgupta, A., Banerjee, P. and Malik, S., Use of microwave irradiation for rapid transesterification of lipids and accelerated synthesis of fatty acyl pyrrolidides for analysis by gas chromatography-mass spectrometry study of fatty acid profiles of olive oil, evening primrose oil, fish oils and phospholipids from mango pulp,... 

In the presence of the corresponding pyrrolidine diamine, the chiral lithium pyrrolidide amide yields dimeric chelates composed of a lithium pyrrolidide amide dimer solvated by a pyrrolidine diamine, (Li-6)2 6, as shown by NMR spectroscopy39. The lithium amide gives two 6Li NMR signals in a 1 1 ratio. The addition of TMEDA to Li-6 results in a similar complex where TMEDA coordinates to the lithium pyrrolidide amide dimer, (Li-6)2 TMEDA. 

In summary, chelating chiral lithium amides exist in either of four major structural motifs or mixtures of them (Scheme 3). Non-coordinating solvents generally favor cyclic trimers, A. Ladder tetramers are favored for pyrrolidide amides in the absence of coordinating solvents. 

Thiocyanat 6-Hydroxy-hexyl- IX 857 Thiokohlensaure -S-ethylester-pyrrolidid E4, 298 (Cl -> SR)... 

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