Showing papers by "Joost N. H. Reek published in 1998"
TL;DR: Two rigid Troger's base dizinc(II) bis-porphyrin receptor molecules and the first generation of dendrimer tetramine 4 form a 2:1 complex as discussed by the authors.
57 citations
TL;DR: The application of a water-soluble diphosphine with a xanthene-type backbone in the biphasic palladium-catalysed hydroxycarbonylation reaction of alkenes leads to the selective formation of carboxylic acids.
50 citations
TL;DR: The conformational behavior and binding properties of various clip-shaped receptor molecules, based on the building block diphenylglycoluril, were studied by NMR, X-ray analysis, and computational techniques.
Abstract: The conformational behavior and binding properties of various clipshaped receptor molecules, based on the building block diphenylglycoluril, were studied by NMR, X-ray analysis, and computational techniques. The conformation and the binding properties of these clips are dependent on the number and type of side walls. Host molecules with two naphthalene side walls and with methoxy groups at the 2- and 7-position are able to bind aromatic guests and silver ions by an induced-fit mechanism.
29 citations
TL;DR: A series of 2-exo-arylfenchyl alcohols (11a−k) was submitted to acid hydrolysis in EtOH/10 M HCl (2:1−1:1, v/v) or with trifluoromethanesulfonic acid (TfOH) (1 equiv) in CHCl3 under varying conditions.
Abstract: A series of 2-exo-arylfenchyl alcohols (11a−k) was submitted to acid hydrolysis in EtOH/10 M HCl (2:1−1:1, v/v) or with trifluoromethanesulfonic acid (TfOH) (1 equiv) in CHCl3 under varying conditions. In all cases, initial formation of the cyclofenchene 12 took place, and after prolonged treatment with acid the reaction proceeded along one of two pathways depending on the nature of the aryl substituent. When the aryl substituent was o-NH2 11b or o-OH 11e, Wagner−Meerwein rearrangement took place to give a carbocationic intermediate 9 that was trapped by the N or O heteroatom to give (2R,4aR,9aR)-9-aza-2,4a-(10,10-dimethylmethano)-1,2,3,4,4a,9a-hexahydro-9a-methyl-9H-fluorene (3b) and (3R,4aR,9bR)-3,9b-(10,10-dimethylmethano)-1,2,3,4,4a,9b-hexahydro-4a-methyldibenzofuran (3c), respectively. In the case of 3c bearing an oxygen heteroatom, equilibration to give the thermodynamic product (1R,4S,4aR,9bR)-1,2,3,4,4a,9b-hexahydro-1,4-methano-1,4a,9b-trimethyldibenzofuran (4a), arising from Nametkin rearrangemen...
20 citations
TL;DR: In this article, the -ac rotamers of 1-(2′-methyl-1′-indenyl)naphthalene-2-carboxylate 6 with 2-methylindenyllithium were obtained.
11 citations
TL;DR: A series of 2-exo-arylfenchyl alcohols (11a−k) was submitted to acid hydrolysis in EtOH/10 M HCl (2:1−1:1, v/v) or with trifluoromethanesulfonic acid (TfOH) (1 equiv) in CHCl3 under varying conditions.
Abstract: A series of 2-exo-arylfenchyl alcohols (11a−k) was submitted to acid hydrolysis in EtOH/10 M HCl (2:1−1:1, v/v) or with trifluoromethanesulfonic acid (TfOH) (1 equiv) in CHCl3 under varying conditions. In all cases, initial formation of the cyclofenchene 12 took place, and after prolonged treatment with acid the reaction proceeded along one of two pathways depending on the nature of the aryl substituent. When the aryl substituent was o-NH2 11b or o-OH 11e, Wagner−Meerwein rearrangement took place to give a carbocationic intermediate 9 that was trapped by the N or O heteroatom to give (2R,4aR,9aR)-9-aza-2,4a-(10,10-dimethylmethano)-1,2,3,4,4a,9a-hexahydro-9a-methyl-9H-fluorene (3b) and (3R,4aR,9bR)-3,9b-(10,10-dimethylmethano)-1,2,3,4,4a,9b-hexahydro-4a-methyldibenzofuran (3c), respectively. In the case of 3c bearing an oxygen heteroatom, equilibration to give the thermodynamic product (1R,4S,4aR,9bR)-1,2,3,4,4a,9b-hexahydro-1,4-methano-1,4a,9b-trimethyldibenzofuran (4a), arising from Nametkin rearrangemen...
TL;DR: In this article, the -ac rotamers of 1-(2′-methyl-1′-indenyl)naphthalene-2-carboxylate 6 with 2-methylindenyllithium were obtained.
Abstract: Reaction of methyl (R)-1-(p-tolylsulfinyl)naphthalene-2-carboxylate 2 with 2-methylindenyllithium affords the -ac rotamer of methyl (S)-1-(2′-methyl-1′-indenyl)naphthalene-2-carboxylate 6 in 63% ee. Heating -ac-6 at 80 °C leads to the formation of an 18:1 mixture of -ac:+sc-6 rotamers, with a barrier to atropisomerisation of ΔG‡353 = 28.4 kcal mol−1 (+sc to -ac). Prototropic rearrangements of the rotamers of 1-(2′-methyl-1′-indenyl)naphthalenes to 1-(2′-methyl-3′-indenyl)naphthalenes occur with retention of the axial stereogenic element.