CuH-Catalyzed Enantioselective Alkylation of Indole Derivatives with Ligand-Controlled Regiodivergence
DC Field | Value | Language |
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dc.contributor.author | Yuxuan Ye | - |
dc.contributor.author | Seoung-Tae Kim | - |
dc.contributor.author | Jinhoon Jeong | - |
dc.contributor.author | Mu-Hyun Baik | - |
dc.contributor.author | Stephen L. Buchwald | - |
dc.date.available | 2019-05-02T08:07:46Z | - |
dc.date.created | 2019-03-19 | - |
dc.date.issued | 2019-03 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | https://pr.ibs.re.kr/handle/8788114/5664 | - |
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. Copyright © 2019 American Chemical Society | - |
dc.description.uri | 1 | - |
dc.language | 영어 | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.title | CuH-Catalyzed Enantioselective Alkylation of Indole Derivatives with Ligand-Controlled Regiodivergence | - |
dc.type | Article | - |
dc.type.rims | ART | - |
dc.identifier.wosid | 000460996500026 | - |
dc.identifier.scopusid | 2-s2.0-85062321926 | - |
dc.identifier.rimsid | 67557 | - |
dc.contributor.affiliatedAuthor | Seoung-Tae Kim | - |
dc.contributor.affiliatedAuthor | Jinhoon Jeong | - |
dc.contributor.affiliatedAuthor | Mu-Hyun Baik | - |
dc.identifier.doi | 10.1021/jacs.8b11838 | - |
dc.identifier.bibliographicCitation | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.141, no.9, pp.3901 - 3909 | - |
dc.citation.title | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.citation.volume | 141 | - |
dc.citation.number | 9 | - |
dc.citation.startPage | 3901 | - |
dc.citation.endPage | 3909 | - |
dc.description.journalClass | 1 | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |