DC Field | Value | Language |
---|---|---|
dc.contributor.author | Ye, Yuxuan | ko |
dc.contributor.author | Kim, Seoung Tae | ko |
dc.contributor.author | Jeong, Jinhoon | ko |
dc.contributor.author | Baik, Mu-Hyun | ko |
dc.contributor.author | Buchwald, Stephen L. | ko |
dc.date.accessioned | 2019-04-15T14:14:59Z | - |
dc.date.available | 2019-04-15T14:14:59Z | - |
dc.date.created | 2019-04-03 | - |
dc.date.issued | 2019-03 | - |
dc.identifier.citation | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.141, no.9, pp.3901 - 3909 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10203/253985 | - |
dc.description.abstract | Enantioenriched molecules bearing indole-substituted stereocenters form a class of privileged compounds in biological, medicinal, and organic chemistry. Thus, the development of methods for asymmetric indole alkylation is highly valuable in organic synthesis. Traditionally, achieving N-selectivity in indole alkylation reactions is a significant challenge, since there is an intrinsic preference for alkylation at C3, the most nucleophilic position. Furthermore, selective and predictable access to either N- or C3-alkylated chiral indoles using catalyst control has been a long-standing goal in indole functionalization. Herein, we report a ligand-controlled regiodivergent synthesis of N- and C3-alkylated chiral indoles that relies on a polarity reversal strategy. In contrast to conventional alkylation reactions in which indoles are employed as nucleophiles, this transformation employs electrophilic indole derivatives, N-(benzoyloxy)indoles, as coupling partners. N- or C3-alkylated indoles are prepared with high levels of regio- and enantioselectivity using a copper hydride catalyst. The regioselectivity is governed by the use of either DTBM-SEGPHOS or Ph-BPE as the supporting ligand. Density functional theory (DFT) calculations are conducted to elucidate the origin of the ligand-controlled regiodivergence. | - |
dc.language | English | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.title | CuH-Catalyzed Enantioselective Alkylation of Indole Derivatives with Ligand-Controlled Regiodivergence | - |
dc.type | Article | - |
dc.identifier.wosid | 000460996500026 | - |
dc.identifier.scopusid | 2-s2.0-85062321926 | - |
dc.type.rims | ART | - |
dc.citation.volume | 141 | - |
dc.citation.issue | 9 | - |
dc.citation.beginningpage | 3901 | - |
dc.citation.endingpage | 3909 | - |
dc.citation.publicationname | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.identifier.doi | 10.1021/jacs.8b11838 | - |
dc.contributor.localauthor | Baik, Mu-Hyun | - |
dc.contributor.nonIdAuthor | Ye, Yuxuan | - |
dc.contributor.nonIdAuthor | Buchwald, Stephen L. | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | NUCLEOPHILIC-SUBSTITUTION REACTION | - |
dc.subject.keywordPlus | ASYMMETRIC HYDROAMINATION | - |
dc.subject.keywordPlus | ALLYLIC ALKYLATION | - |
dc.subject.keywordPlus | N-ALLYLATION | - |
dc.subject.keywordPlus | CHEMISTRY | - |
dc.subject.keywordPlus | REAGENTS | - |
dc.subject.keywordPlus | ALKENES | - |
dc.subject.keywordPlus | AMINES | - |
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