DC Field | Value | Language |
---|---|---|
dc.contributor.author | Kim, YK | - |
dc.contributor.author | Lee, SJ | - |
dc.contributor.author | Ahn, KH | - |
dc.date.accessioned | 2016-03-31T13:25:16Z | - |
dc.date.available | 2016-03-31T13:25:16Z | - |
dc.date.created | 2009-08-13 | - |
dc.date.issued | 2000-11-17 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.other | 2000-OAK-0000001639 | - |
dc.identifier.uri | https://oasis.postech.ac.kr/handle/2014.oak/19787 | - |
dc.description.abstract | Three new hybrid ligands with trans-1,2-diaminocyclohexane backbone have been synthesized from (1R,2R)-2-aminocyclohexylcarbamic acid tert-butyl ester (4), which is prepared through an indirect monoprotection of the diamine. The ligands are (1R,2R)-N-{2-[2-(dimethylamino)benzoyl]amino}-cyclohexyl-2-(diphenylphosphanyl)benzamide and its di-n-butylamino- and diphenylamino-derivatives (3a-c), which belong to formal P,N-type chelates with possible wide bite angles in the metal chelation. To evaluate the new hybrid ligands against well-known P,N- and P,P-chelates (1 and 2), they were employed in the palladium-catalyzed allylic alkylations between two standard racemic allylic acetates, 2-acetoxy-1,3-diphenyl-2-propene (14a) and 2-acetoxy-1,3-dimethyl-2-propene (14b), and dimethyl malonate under different reaction conditions. The catalytic system with the new ligands showed good reactivity toward both the substrates with moderate enantioselectivities (up to 78% ee toward 14a and 80% ee toward 14b). Of particular note, dramatic changes in the sense and in the degree of the enantioselectivity were observed depending on the ligands and reaction conditions, which suggested a different chelation mode was competing with the supposed P,N-chelation mode. An X-ray crystal structure of a chelated palladium complex [Pd(3c)(eta (3)-PhCHCHCHPh)]PF6 was obtained, which showed a P,O-chelation mode in which a carboxamide oxygen acted as the O-ligand. This is the first example of the enantioselective palladium-catalyzed allylic alkylation in which a P,O-chelated complex of a carboxamide group participated as the ligand group. | - |
dc.description.statementofresponsibility | X | - |
dc.language | English | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.relation.isPartOf | JOURNAL OF ORGANIC CHEMISTRY | - |
dc.subject | CONTAINING OXAZOLINE LIGANDS | - |
dc.subject | ASYMMETRIC HYDROSILYLATION | - |
dc.subject | TRANSFER HYDROGENATION | - |
dc.subject | CHIRAL LIGANDS | - |
dc.subject | HECK REACTIONS | - |
dc.subject | PD-COMPLEXES | - |
dc.subject | KETONES | - |
dc.subject | SUBSTITUTION | - |
dc.subject | EFFICIENT | - |
dc.subject | INDUCTION | - |
dc.title | New hybrid ligands with a trans-1,2-diaminocyclohexane backbone: Competing chelation modes in palladium-catalyzed enantioselective allylic alkylation | - |
dc.type | Article | - |
dc.contributor.college | 분자소재융합계의 전자-광 거동연구센터 | - |
dc.identifier.doi | 10.1021/JO000821M | - |
dc.author.google | Kim, YK | - |
dc.author.google | Lee, SJ | - |
dc.author.google | Ahn, KH | - |
dc.relation.volume | 65 | - |
dc.relation.issue | 23 | - |
dc.relation.startpage | 7807 | - |
dc.relation.lastpage | 7813 | - |
dc.contributor.id | 10087916 | - |
dc.relation.journal | JOURNAL OF ORGANIC CHEMISTRY | - |
dc.relation.index | SCI급, SCOPUS 등재논문 | - |
dc.relation.sci | SCI | - |
dc.collections.name | Journal Papers | - |
dc.type.rims | ART | - |
dc.identifier.bibliographicCitation | JOURNAL OF ORGANIC CHEMISTRY, v.65, no.23, pp.7807 - 7813 | - |
dc.identifier.wosid | 000165491300016 | - |
dc.date.tcdate | 2019-01-01 | - |
dc.citation.endPage | 7813 | - |
dc.citation.number | 23 | - |
dc.citation.startPage | 7807 | - |
dc.citation.title | JOURNAL OF ORGANIC CHEMISTRY | - |
dc.citation.volume | 65 | - |
dc.contributor.affiliatedAuthor | Ahn, KH | - |
dc.identifier.scopusid | 2-s2.0-0034680605 | - |
dc.description.journalClass | 1 | - |
dc.description.journalClass | 1 | - |
dc.description.wostc | 57 | - |
dc.description.scptc | 57 | * |
dc.date.scptcdate | 2018-05-121 | * |
dc.type.docType | Article | - |
dc.subject.keywordPlus | CONTAINING OXAZOLINE LIGANDS | - |
dc.subject.keywordPlus | ASYMMETRIC HYDROSILYLATION | - |
dc.subject.keywordPlus | TRANSFER HYDROGENATION | - |
dc.subject.keywordPlus | CHIRAL LIGANDS | - |
dc.subject.keywordPlus | HECK REACTIONS | - |
dc.subject.keywordPlus | PD-COMPLEXES | - |
dc.subject.keywordPlus | KETONES | - |
dc.subject.keywordPlus | SUBSTITUTION | - |
dc.subject.keywordPlus | EFFICIENT | - |
dc.subject.keywordPlus | INDUCTION | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Organic | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.relation.journalResearchArea | Chemistry | - |
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