615249-15-5Relevant academic research and scientific papers
Bi(OTf)3 - A mild catalyst for the synthesis of difficult to obtain C-alkyl substituted glycolurils
Wu, Feng,Mandadapu, Vijaybabu,Day, Anthony I.
, p. 9957 - 9965 (2013)
We have employed Bi(OTf)3 (5 mol %) a catalyst not previously used in the synthesis of urea condensation products from α-dicarbonyl compounds, as a mild method for the synthesis of difficult to obtain glycolurils. There are limited synthetic examples of C-alkylated substituted glycolurils and even fewer carrying functionality on the alkyl substituent. We have successfully synthesised some challenging examples of glycolurils with functionality, which include norbornyl-based structures. The milder reaction conditions enables the isolation of defined intermediate diols and ureas in good yields, and glycolurils are possible, where they would not normally be available under conventional acid catalyzed conditions.
Horse Liver Alcohol Dehydrogenase-catalyzed Enantioselective Reduction of Cyclic Ketones: The Effect of the Hydrophobic Side Chain of the Substrate on the Stereoselectivity of the Reaction
Shigematsu, Hajime,Matsumoto, Toshihiko,Kawauchi, Giichi,Hirose, Yoshiki,Naemura, Koichiro
, p. 3001 - 3008 (2007/10/03)
Horse liver alcohol dehydrogenase (HLADH)-catalyzed enantioselective reductions of alkyl 3-oxocyclopentanecarboxylates, endo-5-acyloxybicycloheptan-2-ones and exo-5-acyloxybicycloheptan-2-ones gave the corresponding homochiral alcohols and ketones and the interaction between the hydrophobic side chain of the substrate and the hydrophobic zone in the active site played an important role in the specificity of the reduction.The stereoselectivities of the reactions were interpreted on the basis of the cubic space section model and a new rule, which contributes to development of a specificity analysis on the basis of the model, is introduced.
Enzymatic Baeyer-Villiger oxidations of some bicycloheptan-2-ones using monooxygenases from Pseudomonas putida NCIMB 10007: enantioselective preparation of a precursor of azadirachtin
Gagnon, Rene,Grogan, Gideon,Roberts, Stanley M.,Villa, Raffaella,Willetts, Andrew J.
, p. 1505 - 1512 (2007/10/02)
Two monooxygenases MO1 (NADH dependent) and MO2 (NADPH dependent) isolated from Ps. putida NCIMB 10007 have been utilized as biocatalysts in Baeyer-Villiger oxidations.The former enzyme oxidized the racemic ketones 9, 10 and 14 into
A Study of the Regioselectivity of Oxygen Insertion in the Baeyer-Villiger Oxidation of Bicycloheptan-2-ones
Hamley, Peter,Holmes, Andrew B.,Marshall, David R.,MacKinnon, John W. M.
, p. 1793 - 1802 (2007/10/02)
Synthesis and Baeyer-Villiger oxidation of the series of bicyclic ketones 3 and 6 is described.The ratio of methine to methylene carbon migration in the oxidation was found to vary depending on the 5-endo and 7-anti substituents of the ketones.Possible re
Synthese und Hydrolyse von 6endo-substituierten p-Toluolsulfonsaeure-estern.
Grob, Cyril A.,Guenther, Bettina,Hanreich, Reinhard
, p. 2288 - 2298 (2007/10/02)
The Synthesis and Hydrolysis of 6endo-Substituted 2endo-Norbornyl p-Toluenesulfonates; The hydrolysis products of the p-toluenesulfonates of several hitherto unknown 6endo-substituted 2endo-norbornanols have been determined.
Die Synthese von 6exo-substituierten p-Toluolsulfonsaeure-estern
Fischer, Walter von,Grob, Cyril A.,Sprecher, Georg von
, p. 806 - 815 (2007/10/02)
A number of hitherto unknown 6exo-substituted 2exo-norbornanols and their p-toluenesulfonates have been prepared by functionalization of intermediate norbornenes.
