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SM ISO690:2012 CURLAT, Serghei, BARBA, Alic, GORINCIOI, Elena, MAKAEV, Fliur. (+)-3-Carene Based Diastereomeric P*-chiral Phosphates. In: Multidisciplinarity in Modern Science for the Benefit of Society, 21-22 septembrie 2017, Chișinău. Chișinău, Republica Moldova: Inst. de Fizică Aplicată, 2017, pp. 43-44. ISBN 978-9975-9787-1-2. |
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Multidisciplinarity in Modern Science for the Benefit of Society 2017 | ||||||
Masa rotundă "Multidisciplinarity in Modern Science for the Benefit of Society" Chișinău, Moldova, 21-22 septembrie 2017 | ||||||
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Pag. 43-44 | ||||||
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(+)-3-Carene based chiral phosphites represent an important type of chirality transfer agents for asymmetric catalysis [1,2]. The most important advantages of phosphite-type ligands include their pronounced π-acidity, oxidation stability, as well as their synthetic availability and low cost. Herein we report the 31P NMR investigation of new synthesized [1] P*-chiral phosphites based on 3carene 1 as one of cheapest natural optically active monoterpene. The 31P NMR spectroscopic data for 2-3 are summarized in Table 1. Compound 2 with NEt2 exocyclic fragment is formed as single stereoisomer, while 3 contain 3% of the second epimer by P* - stereocentre. To estimate steric demands of chiral phosphites, we calculated their Tolman’s angles [3] by the reported method using of semiempirical quantum mechanical AM1 techniques with full optimization of geometrical parameters [4]. The obtained results show that the steric demands of 2,3 vary over a rather wide range between 90° and 122°. |