Please use this identifier to cite or link to this item: https://www.um.edu.mt/library/oar/handle/123456789/24884
Title: First TiCl4-mediated diastereoselective reduction of α-nitro ketones to anti-β-nitro alcohols by BH3·SMe2
Authors: Ballini, Roberto
Bosica, Giovanna
Marcantoni, Enrico
Vita, Patrizia
Bartoli, Giuseppe
Keywords: Nitro compounds
Chemical reactions
Chemistry, Analytic
Issue Date: 2000
Publisher: American Chemical Society
Citation: Ballini, R., Bosica, G., Marcantoni, E., Vita, P., & Bartoli, G. (2000). First TiCl4-mediated diastereoselective reduction of α-nitro ketones to anti-β-nitro alcohols by BH3·SMe2. The Journal of Organic Chemistry, 65(18), 5854-5857.
Abstract: β-Nitro alcohols are an important class of compounds frequently used as key intermediates in the construction of numerous natural products and other useful biologically active compounds. Moreover, they are versatile building blocks in that the nitro group that can be readily reduced with retention of configuration and the resulting amino alcohols are useful intermediates in the elaboration of pharmacologically important products and are also widely used in the preparation of chiral auxiliaries. For these reasons the stereoselective synthesis of β-nitro alcohols continues to be an active area of research. The nitroaldol (Henry) reaction is one of the classical method by which diastereomeric mixtures of β-nitro alcohols are formed upon treatment of primary or secondary nitro alkanes and carbonyl derivatives with a base. Although the Henry reaction has a remarkable ability to yield β-nitro alcohols, the levels of the stereoselectivity are usually low, and, to obtain better diastereoselectivity, it is necessary to carefully control the basicity of the reaction medium or to use complexes as catalysts. Furthermore, in these reactions syn-β-nitro alcohols are often formed predominantly over anti-diastereomers. Thus, in continuation of our interest in the application of nitro aliphatics in synthesis, we decided to investigate the possible formation of â-nitro alcohols by stereoselective reduction of the corresponding R-nitro ketones, readily available from different sources, such as nitro alcohols, alkenes, carboxylic acid derivatives, and ketones
URI: https://www.um.edu.mt/library/oar//handle/123456789/24884
Appears in Collections:Scholarly Works - FacSciChe

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