Remarkable Differences in Reactivity between Benzothiazoline and Hantzsch Ester as a Hydrogen Donor in Chiral Phosphoric Acid Catalyzed Asymmetric Reductive Amination of Ketones
DC Field | Value | Language |
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dc.contributor.author | Kim, Kyung-Hee | - |
dc.contributor.author | Akiyama, Takahiko | - |
dc.contributor.author | Cheon, Cheol-Hong | - |
dc.date.accessioned | 2021-09-04T03:43:41Z | - |
dc.date.available | 2021-09-04T03:43:41Z | - |
dc.date.created | 2021-06-18 | - |
dc.date.issued | 2016-01-20 | - |
dc.identifier.issn | 1861-4728 | - |
dc.identifier.uri | https://scholar.korea.ac.kr/handle/2021.sw.korea/89774 | - |
dc.description.abstract | Described herein are differences in behavior between a Hantzsch ester and a benzothiazoline as hydrogen donors in the chiral phosphoric acid catalyzed asymmetric reductive amination of ketones with p-anisidine. The asymmetric reductive amination of ketones with a Hantzsch ester as a hydrogen donor provided the corresponding chiral amines exclusively, regardless of the structures of the ketones, whereas a similar transformation with a benzothiazoline provided chiral amines and p-methoxyphenyl-protected primary amines in variable yields, depending on the structures of both the ketones and benzothiazolines. Because a benzothiazoline has an N,S-acetal moiety that is vulnerable to p-anisidine, the primary amine can be formed through transimination of the benzothiazoline with p-anisidine followed by reduction of the resulting aldimine with remaining benzothiazoline. | - |
dc.language | English | - |
dc.language.iso | en | - |
dc.publisher | WILEY-V C H VERLAG GMBH | - |
dc.subject | ENANTIOSELECTIVE TRANSFER HYDROGENATION | - |
dc.subject | ORGANOCATALYTIC TRANSFER HYDROGENATION | - |
dc.subject | BRONSTED ACID | - |
dc.subject | KETIMINES | - |
dc.subject | DERIVATIVES | - |
dc.subject | IMINES | - |
dc.subject | ACTIVATION | - |
dc.subject | INDOLINES | - |
dc.subject | SEQUENCE | - |
dc.subject | AMINES | - |
dc.title | Remarkable Differences in Reactivity between Benzothiazoline and Hantzsch Ester as a Hydrogen Donor in Chiral Phosphoric Acid Catalyzed Asymmetric Reductive Amination of Ketones | - |
dc.type | Article | - |
dc.contributor.affiliatedAuthor | Cheon, Cheol-Hong | - |
dc.identifier.doi | 10.1002/asia.201501020 | - |
dc.identifier.scopusid | 2-s2.0-84958910379 | - |
dc.identifier.wosid | 000369064400017 | - |
dc.identifier.bibliographicCitation | CHEMISTRY-AN ASIAN JOURNAL, v.11, no.2, pp.274 - 279 | - |
dc.relation.isPartOf | CHEMISTRY-AN ASIAN JOURNAL | - |
dc.citation.title | CHEMISTRY-AN ASIAN JOURNAL | - |
dc.citation.volume | 11 | - |
dc.citation.number | 2 | - |
dc.citation.startPage | 274 | - |
dc.citation.endPage | 279 | - |
dc.type.rims | ART | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Multidisciplinary | - |
dc.subject.keywordPlus | ENANTIOSELECTIVE TRANSFER HYDROGENATION | - |
dc.subject.keywordPlus | ORGANOCATALYTIC TRANSFER HYDROGENATION | - |
dc.subject.keywordPlus | BRONSTED ACID | - |
dc.subject.keywordPlus | KETIMINES | - |
dc.subject.keywordPlus | DERIVATIVES | - |
dc.subject.keywordPlus | IMINES | - |
dc.subject.keywordPlus | ACTIVATION | - |
dc.subject.keywordPlus | INDOLINES | - |
dc.subject.keywordPlus | SEQUENCE | - |
dc.subject.keywordPlus | AMINES | - |
dc.subject.keywordAuthor | benzothiazolines | - |
dc.subject.keywordAuthor | chiral phosphoric acid catalysis | - |
dc.subject.keywordAuthor | enantioselective reductive amination | - |
dc.subject.keywordAuthor | Hantzsch ester | - |
dc.subject.keywordAuthor | organic hydrogen donor | - |
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