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Synthesis and stereochemical assignments of diastereomeric Ni(II) complexes of glycine Schiff base with (R)-2-(N-{2-[N-alkyl-N-(1-phenylethyl)-amino]acetyl}amino) benzophenone; a case of configurationally stable stereogenic nitrogen

dc.contributor.authorMoriwaki, Hiroki
dc.contributor.authorResch, Daniel
dc.contributor.authorLi, Hengguang
dc.contributor.authorOjima, Iwao
dc.contributor.authorTakeda, Ryosuke
dc.contributor.authorAceña Bonilla, José Luis
dc.contributor.authorSoloshonok, Vadym Anatolievch ORCID
dc.date.accessioned2016-02-18T15:03:25Z
dc.date.available2016-02-18T15:03:25Z
dc.date.issued2014-02-19
dc.identifier.citationBeilstein Journal of Organic Chemistry 10 : 442-448 (2014)es
dc.identifier.issn1860-5397
dc.identifier.urihttp://hdl.handle.net/10810/17388
dc.description.abstractA family of chiral ligands derived from alpha-phenylethylamine and 2-aminobenzophenone were prepared by alkylation of the nitrogen atom. Upon reaction with glycine and a Ni(II) salt, these ligands were transformed into diastereomeric complexes, as a result of the configurational stability of the stereogenic nitrogen atom. Different diastereomeric ratios were observed depending on the substituent R introduced in the starting ligand, and stereochemical assignments were based on X-ray analysis, along with NMR studies and optical rotation measurements.es
dc.description.sponsorshipWe thank IKERBASQUE, Basque Foundation for Science; the Basque Government (SAIOTEK S-PE12UN044), Spanish Ministry of Science and Innovation (CTQ2010-19974) and Hamari Chemicals (Osaka, Japan) for generous financial support. The Stony Brook University single-crystal diffractometer was obtained through the support of the National Science Foundation (NSF) grant CHE-0840483. JLA and VAS are very grateful to Professor Dieter Seebach (ETH-Zurich) for fruitful and inspirational discussions.es
dc.language.isoenges
dc.publisherBeilstein Institutes
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.subjectamino acids; ; ; ; stereogenic nitrogenes
dc.subjectasymmetric synthesises
dc.subjectNi(II) complexeses
dc.subjectSchiff baseses
dc.subjectstereogenic nitrogenes
dc.subjectalpha-amino-acidses
dc.subjectmichael-addition-reactionses
dc.subjectsubstituted pyroglutamic acidses
dc.subjectefficient asymmetric-synthesises
dc.subjectphase-transfer catalystses
dc.subjectvirtually complete controles
dc.subjectalkyl alhide alkylationses
dc.subjectlarge-scale synthesises
dc.subjectnucleophilic glycinees
dc.subjectaldol reactionses
dc.titleSynthesis and stereochemical assignments of diastereomeric Ni(II) complexes of glycine Schiff base with (R)-2-(N-{2-[N-alkyl-N-(1-phenylethyl)-amino]acetyl}amino) benzophenone; a case of configurationally stable stereogenic nitrogenes
dc.typeinfo:eu-repo/semantics/articlees
dc.rights.holder2014 Moriwaki et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)es
dc.relation.publisherversionhttp://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-10-41es
dc.identifier.doi10.3762/bjoc.10.41
dc.departamentoesQuímica orgánica Ies_ES
dc.departamentoeuKimika organikoa Ies_ES
dc.subject.categoriaCHEMISTRY, ORGANIC


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