Disrotatory Ring-Opening of Furans Gives Stereocontrol

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dc.contributor.authorJeong, Jinhoonko
dc.contributor.authorKim, Hyunjoongko
dc.contributor.authorHazra, Chinmoy K.ko
dc.contributor.authorChang, Sukbokko
dc.contributor.authorBaik, Mu-Hyunko
dc.date.accessioned2019-10-10T06:20:05Z-
dc.date.available2019-10-10T06:20:05Z-
dc.date.created2019-10-07-
dc.date.created2019-10-07-
dc.date.created2019-10-07-
dc.date.created2019-10-07-
dc.date.issued2019-09-
dc.identifier.citationTHE JOURNAL OF ORGANIC CHEMISTRY, v.84, no.17, pp.11061 - 11067-
dc.identifier.issn0022-3263-
dc.identifier.urihttp://hdl.handle.net/10203/267887-
dc.description.abstractThe ring-opening of 2-methylfuran and 2,3-dihydro-5-methylfuran catalyzed by the Lewis acid catalyst tris(pentafluorophenyl)borane in the presence of hydrosilanes was studied using quantum chemical methods. In a previous study, it was suggested that the stereoselective formation of the product is due to a nucleophilic vinylic substitution (SNV) during the reaction. Our calculations show that the pathway involving the SNV reaction is energetically not accessible. Instead, the intramolecular C-O bond cleavage is found to be much more favorable in energy for the ring opening reaction. The experimentally observed excellent stereoselectivity toward the Z-isomer product originates from an intrinsic preference of the furan ring to couple the C-O bond cleavage with a disrotatory motion of the oxygen and carbon fragments. This stereoselective feature is naturally programmed into the furan ring manifold and should be generally exploitable for engineering stereoselective ring-opening processes of bioderived furans.-
dc.languageEnglish-
dc.publisherAMER CHEMICAL SOC-
dc.titleDisrotatory Ring-Opening of Furans Gives Stereocontrol-
dc.typeArticle-
dc.identifier.wosid000485089200050-
dc.identifier.scopusid2-s2.0-85071998463-
dc.type.rimsART-
dc.citation.volume84-
dc.citation.issue17-
dc.citation.beginningpage11061-
dc.citation.endingpage11067-
dc.citation.publicationnameTHE JOURNAL OF ORGANIC CHEMISTRY-
dc.identifier.doi10.1021/acs.joc.9b01627-
dc.contributor.localauthorChang, Sukbok-
dc.contributor.localauthorBaik, Mu-Hyun-
dc.contributor.nonIdAuthorHazra, Chinmoy K.-
dc.description.isOpenAccessN-
dc.type.journalArticleArticle-
dc.subject.keywordPlusSOLVATION FREE-ENERGIES-
dc.subject.keywordPlusBIOMASS-
dc.subject.keywordPlusCONVERSION-
dc.subject.keywordPlusTHERMOCHEMISTRY-
dc.subject.keywordPlusREDUCTION-
dc.subject.keywordPlusCHEMICALS-
dc.subject.keywordPlusALCOHOLS-
dc.subject.keywordPlusSILICON-
dc.subject.keywordPlusETHERS-
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