Full metadata record
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Lee, Hanseul | ko |
dc.contributor.author | Cho, Soohong | ko |
dc.contributor.author | Lee, Yunmi | ko |
dc.contributor.author | Jung, Byunghyuck | ko |
dc.date.accessioned | 2021-01-22T07:37:27Z | - |
dc.date.available | 2021-01-22T07:37:27Z | - |
dc.date.created | 2020-10-29 | - |
dc.date.issued | 2020-10 | - |
dc.identifier.citation | Journal of Organic Chemistry, v.85, no.19, pp.12024 - 12035 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/20.500.11750/12813 | - |
dc.description.abstract | An efficient and stereoselective method for the synthesis of (E)- and (Z)-alpha-silyl-alpha,beta-unsaturated amides and its synthetic applications are presented herein. The solvent-controlled hydroaluminations of Si-substituted alkynes with DIBAL-H generate diastereomerically enriched alkenylaluminum reagents that are directly reacted with isocyanates at ambient temperature to afford alpha-silyl-alpha,beta-unsaturated amides in high yields with retained stereoselectivity. In particular, this process enables the synthesis of a broad range of (E)-alpha-silyl-alpha,beta-unsaturated amides, which are the less studied isomers. The synthetic utility of this method is highlighted by its short reaction time, ease of purification, easily accessible substrates and reagents, gram-scale synthesis, and the further transformations of C-Si bonds into C-H, C-X, and C-C bonds. © 2020 American Chemical Society. | - |
dc.language | English | - |
dc.publisher | American Chemical Society | - |
dc.title | Stereoselective Formal Hydroamidation of Si-Substituted Arylacetylenes with DIBAL-H and Isocyanates: Synthesis of (E)- and (Z)-alpha-Silyl-alpha,beta-unsaturated Amides | - |
dc.type | Article | - |
dc.identifier.doi | 10.1021/acs.joc.0c01903 | - |
dc.identifier.wosid | 000577156600003 | - |
dc.identifier.scopusid | 2-s2.0-85095569206 | - |
dc.type.local | Article(Overseas) | - |
dc.type.rims | ART | - |
dc.description.journalClass | 1 | - |
dc.contributor.nonIdAuthor | Lee, Hanseul | - |
dc.contributor.nonIdAuthor | Cho, Soohong | - |
dc.contributor.nonIdAuthor | Lee, Yunmi | - |
dc.identifier.citationVolume | 85 | - |
dc.identifier.citationNumber | 19 | - |
dc.identifier.citationStartPage | 12024 | - |
dc.identifier.citationEndPage | 12035 | - |
dc.identifier.citationTitle | Journal of Organic Chemistry | - |
dc.type.journalArticle | Article | - |
dc.description.isOpenAccess | N | - |
dc.subject.keywordPlus | ALKYNES | - |
dc.subject.keywordPlus | CAFFEIC ACID-AMIDES | - |
dc.subject.keywordPlus | ALPHA,BETA-UNSATURATED AMIDES | - |
dc.subject.keywordPlus | CATALYZED SYNTHESIS | - |
dc.subject.keywordPlus | CHIRAL AUXILIARY | - |
dc.subject.keywordPlus | BOND FORMATION | - |
dc.subject.keywordPlus | AMINOCARBONYLATION | - |
dc.subject.keywordPlus | AVENANTHRAMIDES | - |
dc.subject.keywordPlus | CARBONYLATION | - |
dc.subject.keywordPlus | REAGENTS | - |
dc.contributor.affiliatedAuthor | Jung, Byunghyuck | - |
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