DC Field | Value | Language |
---|---|---|
dc.contributor.author | Boylan, Amy | ko |
dc.contributor.author | Nguyen, Thien S. | ko |
dc.contributor.author | Lundy, Brian J. | ko |
dc.contributor.author | Li, Jian-Yuan | ko |
dc.contributor.author | Vallakati, Ravikrishna | ko |
dc.contributor.author | Sundstrom, Sasha | ko |
dc.contributor.author | May, Jeremy A. | ko |
dc.date.accessioned | 2021-05-25T08:10:08Z | - |
dc.date.available | 2021-05-25T08:10:08Z | - |
dc.date.created | 2021-05-25 | - |
dc.date.created | 2021-05-25 | - |
dc.date.created | 2021-05-25 | - |
dc.date.issued | 2021-03 | - |
dc.identifier.citation | MOLECULES, v.26, no.6 | - |
dc.identifier.issn | 1420-3049 | - |
dc.identifier.uri | http://hdl.handle.net/10203/285340 | - |
dc.description.abstract | Two key factors bear on reaction rates for the conjugate addition of alkenyl boronic acids to heteroaryl-appended enones: the proximity of inductively electron-withdrawing heteroatoms to the site of bond formation and the resonance contribution of available heteroatom lone pairs to stabilize the developing positive charge at the enone beta-position. For the former, the closer the heteroatom is to the enone beta-carbon, the faster the reaction. For the latter, greater resonance stabilization of the benzylic cationic charge accelerates the reaction. Thus, reaction rates are increased by the closer proximity of inductive electron-withdrawing elements, but if resonance effects are involved, then increased rates are observed with electron-donating ability. Evidence for these trends in isomeric substrates is presented, and the application of these insights has allowed for reaction conditions that provide improved reactivity with previously problematic substrates. | - |
dc.language | English | - |
dc.publisher | MDPI | - |
dc.title | Rate Dependence on Inductive and Resonance Effects for the Organocatalyzed Enantioselective Conjugate Addition of Alkenyl and Alkynyl Boronic Acids to beta-Indolyl Enones and beta-Pyrrolyl Enones | - |
dc.type | Article | - |
dc.identifier.wosid | 000645432600001 | - |
dc.identifier.scopusid | 2-s2.0-85103920165 | - |
dc.type.rims | ART | - |
dc.citation.volume | 26 | - |
dc.citation.issue | 6 | - |
dc.citation.publicationname | MOLECULES | - |
dc.identifier.doi | 10.3390/molecules26061615 | - |
dc.contributor.localauthor | Nguyen, Thien S. | - |
dc.contributor.nonIdAuthor | Boylan, Amy | - |
dc.contributor.nonIdAuthor | Lundy, Brian J. | - |
dc.contributor.nonIdAuthor | Li, Jian-Yuan | - |
dc.contributor.nonIdAuthor | Vallakati, Ravikrishna | - |
dc.contributor.nonIdAuthor | Sundstrom, Sasha | - |
dc.contributor.nonIdAuthor | May, Jeremy A. | - |
dc.description.isOpenAccess | Y | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordAuthor | enantioselective conjugate addition | - |
dc.subject.keywordAuthor | heterocycles | - |
dc.subject.keywordAuthor | pyrrole | - |
dc.subject.keywordAuthor | indole | - |
dc.subject.keywordPlus | FRIEDEL-CRAFTS ALKYLATION | - |
dc.subject.keywordPlus | ETHERATE MEDIATED 1,4-ADDITION | - |
dc.subject.keywordPlus | CATALYZED ASYMMETRIC ADDITION | - |
dc.subject.keywordPlus | C-H BONDS | - |
dc.subject.keywordPlus | STEREOSELECTIVE-SYNTHESIS | - |
dc.subject.keywordPlus | QUATERNARY STEREOCENTERS | - |
dc.subject.keywordPlus | HYDROXYBENZYL ALCOHOLS | - |
dc.subject.keywordPlus | 3-SUBSTITUTED INDOLES | - |
dc.subject.keywordPlus | MICHAEL ADDITION | - |
dc.subject.keywordPlus | DERIVATIVES | - |
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