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dc.contributor.author | Metlushka K. | |
dc.contributor.author | Sadkova D. | |
dc.contributor.author | Shaimardanova L. | |
dc.contributor.author | Nikitina K. | |
dc.contributor.author | Tufatullin A. | |
dc.contributor.author | Kataeva O. | |
dc.contributor.author | Alfonsov V. | |
dc.date.accessioned | 2018-09-18T20:17:43Z | |
dc.date.available | 2018-09-18T20:17:43Z | |
dc.date.issued | 2014 | |
dc.identifier.issn | 1066-5285 | |
dc.identifier.uri | https://dspace.kpfu.ru/xmlui/handle/net/138408 | |
dc.description.abstract | © 2014 Springer Science+Business Media New York. A reaction of triethyl phosphite with 3-alkyl-1-phenylnaphthoxazines in the presence of halotrimethylsilanes with subsequent removal of the trimethylsilyl group by hydrolysis furnished diastereomeric α-aminoalkylphosphonic derivatives of Betti base. The highest diastereomeric excess was observed in the reaction with bromotrimethylsilane at low temperature. In the case of 3-isobutyl-1-phenylnaphthoxazine, a major diastereomer was isolated from the reaction mixture by crystallization. X-ray diffraction analysis was used to establish relative configuration of its chiral centers. This method can be also used for the preparation of α-aminobenzylphosphonic derivatives, which was shown using 1,3-diphenylnaphthoxazine as an example. Major diastereomers of α-aminobenzyl- and α-aminoalkylphosphonic acid derivatives of Betti base obtained according to this procedure have different relative configurations of their chiral centers. | |
dc.relation.ispartofseries | Russian Chemical Bulletin | |
dc.subject | 3-alkyl-1-phenylnaphthoxazines | |
dc.subject | asymmetric induction | |
dc.subject | Betti base | |
dc.subject | halosilanes | |
dc.subject | triethyl phosphite | |
dc.subject | α-aminoalkylphosphonates | |
dc.title | Diastereoselective synthesis of α-aminoalkylphosphonic acid derivatives of Betti base | |
dc.type | Article | |
dc.relation.ispartofseries-issue | 6 | |
dc.relation.ispartofseries-volume | 63 | |
dc.collection | Публикации сотрудников КФУ | |
dc.relation.startpage | 1390 | |
dc.source.id | SCOPUS10665285-2014-63-6-SID84924240958 |