DC Field | Value | Language |
---|---|---|
dc.contributor.author | Ham, Jin Su | ko |
dc.contributor.author | Park, Bohyun | ko |
dc.contributor.author | Son, Mina | ko |
dc.contributor.author | Roque, Jose B. | ko |
dc.contributor.author | Jurczyk, Justin | ko |
dc.contributor.author | Yeung, Charles S. | ko |
dc.contributor.author | Baik, Mu-Hyun | ko |
dc.contributor.author | Sarpong, Richmond | ko |
dc.date.accessioned | 2020-08-31T08:55:29Z | - |
dc.date.available | 2020-08-31T08:55:29Z | - |
dc.date.created | 2020-08-14 | - |
dc.date.created | 2020-08-14 | - |
dc.date.created | 2020-08-14 | - |
dc.date.issued | 2020-07 | - |
dc.identifier.citation | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.142, no.30, pp.13041 - 13050 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10203/276053 | - |
dc.description.abstract | Herein we report the synthesis of substituted indolizidines and related N-fused bicycles from simple saturated cyclic amines through sequential C-H and C-C bond functionalizations. Inspired by the Norrish-Yang Type II reaction, C-H functionalization of azacycles is achieved by forming alpha-hydroxy-beta-lactams from precursor alpha-ketoamide derivatives under mild, visible light conditions. Selective cleavage of the distal C(sp(2))-C(sp(3)) bond in alpha-hydroxy-beta-lactams using a Rh-complex leads to alpha-acyl intermediates which undergo sequential Rh-catalyzed decarbonylation, 1,4-addition to an electrophile, and aldol cyclization, to afford N-fused bicycles including indolizidines. Computational studies provide mechanistic insight into the observed positional selectivity of C-C cleavage, which depends strongly on the groups bound to Rh trans to the phosphine ligand. | - |
dc.language | English | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.title | C-H/C-C Functionalization Approach to N-Fused Heterocycles from Saturated Azacycles | - |
dc.type | Article | - |
dc.identifier.wosid | 000557854400018 | - |
dc.identifier.scopusid | 2-s2.0-85089615809 | - |
dc.type.rims | ART | - |
dc.citation.volume | 142 | - |
dc.citation.issue | 30 | - |
dc.citation.beginningpage | 13041 | - |
dc.citation.endingpage | 13050 | - |
dc.citation.publicationname | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.identifier.doi | 10.1021/jacs.0c04278 | - |
dc.contributor.localauthor | Baik, Mu-Hyun | - |
dc.contributor.nonIdAuthor | Ham, Jin Su | - |
dc.contributor.nonIdAuthor | Roque, Jose B. | - |
dc.contributor.nonIdAuthor | Jurczyk, Justin | - |
dc.contributor.nonIdAuthor | Yeung, Charles S. | - |
dc.contributor.nonIdAuthor | Sarpong, Richmond | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | BOND ACTIVATION | - |
dc.subject.keywordPlus | II REACTIONS | - |
dc.subject.keywordPlus | CLEAVAGE | - |
dc.subject.keywordPlus | ALPHA | - |
dc.subject.keywordPlus | INDOLIZIDINE | - |
dc.subject.keywordPlus | ALKALOIDS | - |
dc.subject.keywordPlus | MOLECULES | - |
dc.subject.keywordPlus | ARYLATION | - |
dc.subject.keywordPlus | STRATEGY | - |
dc.subject.keywordPlus | HYDROGEN | - |
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