100476-16-2Relevant academic research and scientific papers
Lipase-mediated resolution of substituted 2-aryl-propanols: Application to the enantioselective synthesis of phenolic sesquiterpenes
Serra, Stefano
experimental part, p. 619 - 628 (2011/07/08)
A comprehensive study of the lipase-mediated resolution of substituted 2-aryl-propanols is reported. The latter alcohols were submitted to the irreversible acetylation catalyzed either by PPL, CRL, or lipase PS. The enantioselectivity of these transformations was dependent on the type of lipase used. The type of substituents and particularly their position on the aromatic ring strongly affected the selectivity of the reaction. The experiments described prove that PPL is the more versatile lipase catalyzing the acetylation with an enantiomeric ratio (E) value that ranges from 1 up to 144, depending on the substrate used. Conversely, the same transformations were catalyzed by CRL and lipase PS with an enantiomeric ratio value, which is always less than 5. The remarkable behavior of PPL was exploited in the large scale resolution of some substituted 2-aryl-propanols whose enantiomeric forms are relevant building blocks in the enantioselective synthesis of phenolic sesquiterpenes. By these means, the synthesis of (S)-turmeronol B and the formal syntheses of (R)-curcumene, (R)-curcuphenol, (R)-xanthorrhizol, and (R)-curcuhydroquinone were accomplished.
Non-photochemical rearrangements of o-nitrobenzyl compounds
Corrie, John E. T.,Gradwell, Michael J.,Papageorgiou, George
, p. 2977 - 2982 (2007/10/03)
Three rearrangements of 2-nitrobenzyl compounds with increasingly complex structural changes are described. The first is a remarkably facile conversion of 2-nitrobenzyl triflate to 2-nitrosobenzaldehyde. The second is an unexpected formation of 1-acetyl-2
Hydroxyalkylation, Acylation, Formylation, and Carboxylation of 2-Nitro- and 2-Chloro-1-(trimethylsilyl)benzene
Effenberger, Franz,Spiegler, Wolfgang
, p. 3900 - 3914 (2007/10/02)
The synthetic application of base-catalyzed carbodesilylation of aryltrimethylsilanes is demonstrated in the reactions of 2-nitro- (1a) and 2-chloro-1-(trimethylsilyl)benzene (1b) with aldehydes, ketones, acyl fluorides and carboxylic anhydrides, respectively, dimethylformamide, and carbon dioxide.The corresponding benzenes 3 and 8, (hydroxyalkyl)benzenes 4, 6, and 9, the benzophenones 12, the benzaldehydes 14, and the benzoic acids 17 are obtained in good yields.The new method is a useful alternative to the normal electrophilic substitution or the application of organometallic compounds, respectively, for the synthesis of polysubstituted benzenes.
