DC Field | Value | Language |
---|---|---|
dc.contributor.author | Lee, Geun Seok | ko |
dc.contributor.author | Park, Beomsoon | ko |
dc.contributor.author | Hong, Soon Hyeok | ko |
dc.date.accessioned | 2022-09-19T09:01:04Z | - |
dc.date.available | 2022-09-19T09:01:04Z | - |
dc.date.created | 2022-09-19 | - |
dc.date.created | 2022-09-19 | - |
dc.date.issued | 2022-09 | - |
dc.identifier.citation | NATURE COMMUNICATIONS, v.13, no.1 | - |
dc.identifier.issn | 2041-1723 | - |
dc.identifier.uri | http://hdl.handle.net/10203/298634 | - |
dc.description.abstract | Chiral alpha-amino ketones are privileged motifs in bioorganic and medicinal chemistry. Here, the authors develop an efficient method to synthesize these structures via stereoretentive direct cross-coupling of amino acid chlorides with simple aliphatic substrates. The direct modification of naturally occurring chiral amino acids to their amino ketone analogs is a significant synthetic challenge. Here, an efficient and robust cross-coupling reaction between chiral amino acid chlorides and unactivated C(sp(3))-H hydrocarbons is achieved by a mechanistically designed Ni/Ir photoredox catalysis. This reaction, which proceeds under mild conditions, enables modular access to a wide variety of chiral amino ketones that retain the stereochemistry of the starting amino acids. In-depth mechanistic analysis reveals that the strategic generation of an N-acyllutidinium intermediate is critical for the success of this reaction. The barrierless reduction of the N-acyllutidinium intermediate facilitates the delivery of chiral amino ketones with retention of stereochemistry. This pathway avoids the formation of a detrimental nickel intermediate, which could be responsible for undesirable decarbonylation and transmetalation reactions that limit the utility of previously reported methods. | - |
dc.language | English | - |
dc.publisher | NATURE PORTFOLIO | - |
dc.title | Stereoretentive cross-coupling of chiral amino acid chlorides and hydrocarbons through mechanistically controlled Ni/Ir photoredox catalysis | - |
dc.type | Article | - |
dc.identifier.wosid | 000849494300002 | - |
dc.identifier.scopusid | 2-s2.0-85137164092 | - |
dc.type.rims | ART | - |
dc.citation.volume | 13 | - |
dc.citation.issue | 1 | - |
dc.citation.publicationname | NATURE COMMUNICATIONS | - |
dc.identifier.doi | 10.1038/s41467-022-32851-7 | - |
dc.contributor.localauthor | Hong, Soon Hyeok | - |
dc.contributor.nonIdAuthor | Lee, Geun Seok | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | PEPTIDYL KETONES | - |
dc.subject.keywordPlus | THIOL ESTERS | - |
dc.subject.keywordPlus | BOND | - |
dc.subject.keywordPlus | PHOTOELIMINATION | - |
dc.subject.keywordPlus | ELECTROPHILES | - |
dc.subject.keywordPlus | COMPLEXES | - |
dc.subject.keywordPlus | CHEMISTRY | - |
dc.subject.keywordPlus | ACYLATION | - |
dc.subject.keywordPlus | NICKEL | - |
dc.subject.keywordPlus | POTENT | - |
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