DC Field | Value | Language |
---|---|---|
dc.contributor.author | McAtee, Christopher C. | ko |
dc.contributor.author | Nasrallah, Daniel J. | ko |
dc.contributor.author | Ryu, Ho | ko |
dc.contributor.author | Gatazka, Michael R. | ko |
dc.contributor.author | McAtee, Rory C. | ko |
dc.contributor.author | Baik, Mu-Hyun | ko |
dc.contributor.author | Schindler, Corinna S. | ko |
dc.date.accessioned | 2023-03-22T06:01:09Z | - |
dc.date.available | 2023-03-22T06:01:09Z | - |
dc.date.created | 2023-03-13 | - |
dc.date.created | 2023-03-13 | - |
dc.date.created | 2023-03-13 | - |
dc.date.created | 2023-03-13 | - |
dc.date.issued | 2023-02 | - |
dc.identifier.citation | ACS CATALYSIS, v.13, no.5, pp.3036 - 3043 | - |
dc.identifier.issn | 2155-5435 | - |
dc.identifier.uri | http://hdl.handle.net/10203/305725 | - |
dc.description.abstract | Cyclopentadienes are scaffolds in organometallic chemistry, synthetic organic chemistry, and catalysis. We herein describe a regioselective Lewis-acid-catalyzed method for the synthesis of highly functionalized cyclo-pentadienes incorporating electronically and sterically diverse subunits. Our experimental and theoretical investigations support a mechanism that is related to catalytic carbonyl-olefin metathesis reactions wherein Lewis-acid-catalyzed cyclo-additions between carbonyl and alkene functionalities afford reactive oxetane intermediates. However, in lieu of a [2+2]-cycloreversion, stepwise oxetane fragmentation to intermediate carbocations results in the formation of function-alized cyclopentadienes via interrupted carbonyl-olefin metathesis. This work provides insights into the design of catalytic carbonyl-olefin metathesis reactions of aliphatic ketone substrates as stepwise oxetane fragmentation was previously only reported as a competing reaction pathway for aryl ketones. | - |
dc.language | English | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.title | Catalytic, Interrupted Carbonyl-Olefin Metathesis for the Formation of Functionalized Cyclopentadienes | - |
dc.type | Article | - |
dc.identifier.wosid | 000944484400001 | - |
dc.identifier.scopusid | 2-s2.0-85148356769 | - |
dc.type.rims | ART | - |
dc.citation.volume | 13 | - |
dc.citation.issue | 5 | - |
dc.citation.beginningpage | 3036 | - |
dc.citation.endingpage | 3043 | - |
dc.citation.publicationname | ACS CATALYSIS | - |
dc.identifier.doi | 10.1021/acscatal.2c055353036 | - |
dc.contributor.localauthor | Baik, Mu-Hyun | - |
dc.contributor.nonIdAuthor | McAtee, Christopher C. | - |
dc.contributor.nonIdAuthor | Nasrallah, Daniel J. | - |
dc.contributor.nonIdAuthor | Gatazka, Michael R. | - |
dc.contributor.nonIdAuthor | McAtee, Rory C. | - |
dc.contributor.nonIdAuthor | Schindler, Corinna S. | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordAuthor | Lewis acid catalysis | - |
dc.subject.keywordAuthor | carbonyl-olefin metathesis | - |
dc.subject.keywordAuthor | cyclopentadienes | - |
dc.subject.keywordAuthor | catalysis | - |
dc.subject.keywordAuthor | interrupted | - |
dc.subject.keywordPlus | DIELS-ALDER REACTIONS | - |
dc.subject.keywordPlus | SUBSTITUTED CYCLOPENTADIENES | - |
dc.subject.keywordPlus | GOLD(I)-CATALYZED SYNTHESIS | - |
dc.subject.keywordPlus | SIDE-CHAIN | - |
dc.subject.keywordPlus | COMPLEXES | - |
dc.subject.keywordPlus | DERIVATIVES | - |
dc.subject.keywordPlus | CHEMISTRY | - |
dc.subject.keywordPlus | ALKENES | - |
dc.subject.keywordPlus | WATER | - |
dc.subject.keywordPlus | ACID | - |
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