DC Field | Value | Language |
---|---|---|
dc.contributor.author | Ylagan, Ridge Michael P. | ko |
dc.contributor.author | Lee, Eric Jaewon | ko |
dc.contributor.author | Negru, Daniela E. | ko |
dc.contributor.author | Ricci, Paolo | ko |
dc.contributor.author | Park, Bohyun | ko |
dc.contributor.author | Ryu, Haram | ko |
dc.contributor.author | Baik, Mu-Hyun | ko |
dc.contributor.author | Evans, P. Andrew | ko |
dc.date.accessioned | 2023-06-07T07:00:24Z | - |
dc.date.available | 2023-06-07T07:00:24Z | - |
dc.date.created | 2023-05-30 | - |
dc.date.issued | 2023-06 | - |
dc.identifier.citation | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.62, no.23 | - |
dc.identifier.issn | 1433-7851 | - |
dc.identifier.uri | http://hdl.handle.net/10203/307087 | - |
dc.description.abstract | An enantioselective rhodium(I)-catalyzed Pauson-Khand reaction (PKR) using 1,6-chloroenynes that contain challenging 1,1-disubstituted olefins is described. In contrast to the previous studies with these types of substrates, which are only suitable for a single type of tether and alkyne substituent, the new approach results in a more expansive substrate scope, including carbon and heteroatom tethers with polar and non-polar substituents on the alkene. DFT calculations provide critical insight into the role of the halide, which pre-polarizes the alkyne to lower the barrier for metallacycle formation and provides the proper steric profile to promote a favorable enantiodetermining interaction between substrate and chiral diphosphine ligand. Hence, the chloroalkyne enables the efficient and enantioselective PKR with 1,6-enynes that contain challenging 1,1-disubstituted olefins, thereby representing a new paradigm for enantioselective reactions involving 1,6-enynes. | - |
dc.language | English | - |
dc.publisher | WILEY-V C H VERLAG GMBH | - |
dc.title | Enantioselective Rhodium-Catalyzed Pauson-Khand Reactions of 1,6-Chloroenynes with 1,1-Disubstituted Olefins | - |
dc.type | Article | - |
dc.identifier.wosid | 000977827700001 | - |
dc.identifier.scopusid | 2-s2.0-85153719697 | - |
dc.type.rims | ART | - |
dc.citation.volume | 62 | - |
dc.citation.issue | 23 | - |
dc.citation.publicationname | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | - |
dc.identifier.doi | 10.1002/anie.202300211 | - |
dc.contributor.localauthor | Baik, Mu-Hyun | - |
dc.contributor.nonIdAuthor | Ylagan, Ridge Michael P. | - |
dc.contributor.nonIdAuthor | Lee, Eric Jaewon | - |
dc.contributor.nonIdAuthor | Negru, Daniela E. | - |
dc.contributor.nonIdAuthor | Ricci, Paolo | - |
dc.contributor.nonIdAuthor | Evans, P. Andrew | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordAuthor | Chloroenyne | - |
dc.subject.keywordAuthor | DFT Calculations | - |
dc.subject.keywordAuthor | Enantioselectivity | - |
dc.subject.keywordAuthor | Pauson-Khand Reaction | - |
dc.subject.keywordAuthor | Quaternary Stereocenter | - |
dc.subject.keywordPlus | EFFECTIVE CORE POTENTIALS | - |
dc.subject.keywordPlus | CHIRAL PHOSPHINE-LIGANDS | - |
dc.subject.keywordPlus | SOLVATION FREE-ENERGIES | - |
dc.subject.keywordPlus | MOLECULAR CALCULATIONS | - |
dc.subject.keywordPlus | BASIS-SETS | - |
dc.subject.keywordPlus | CYCLOCARBONYLATION | - |
dc.subject.keywordPlus | CYCLIZATION | - |
dc.subject.keywordPlus | MECHANISM | - |
dc.subject.keywordPlus | MODEL | - |
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