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- Publisher Website: 10.1126/science.1249198
- Scopus: eid_2-s2.0-84896050363
- PMID: 24626923
- WOS: WOS:000332728500029
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Article: Ligand-controlled C(sp3)-H arylation and olefination in synthesis of unnatural chiral α-amino acids
Title | Ligand-controlled C(sp3)-H arylation and olefination in synthesis of unnatural chiral α-amino acids |
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Authors | |
Issue Date | 2014 |
Citation | Science, 2014, v. 343, n. 6176, p. 1216-1220 How to Cite? |
Abstract | The use of ligands to tune the reactivity and selectivity of transition metal catalysts for C(sp3)-H bond functionalization is a central challenge in synthetic organic chemistry. Herein, we report a rare example of catalyst-controlled C(sp3)-H arylation using pyridine and quinoline derivatives: The former promotes exclusive monoarylation, whereas the latter activates the catalyst further to achieve diarylation. Successive application of these ligands enables the sequential diarylation of a methyl group in an alanine derivative with two different aryl iodides, affording a wide range of β-Ar-β-Ar?-α-amino acids with excellent levels of diastereoselectivity (diastereomeric ratio > 20:1). Both configurations of the β-chiral center can be accessed by choosing the order in which the aryl groups are installed. The use of a quinoline derivative as a ligand also enables C(sp3)-H olefination of a protected alanine. |
Persistent Identifier | http://hdl.handle.net/10722/276981 |
ISSN | 2023 Impact Factor: 44.7 2023 SCImago Journal Rankings: 11.902 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | He, Jian | - |
dc.contributor.author | Li, Suhua | - |
dc.contributor.author | Deng, Youqian | - |
dc.contributor.author | Fu, Haiyan | - |
dc.contributor.author | Laforteza, Brian N. | - |
dc.contributor.author | Spangler, Jillian E. | - |
dc.contributor.author | Homs, Anna | - |
dc.contributor.author | Yu, Jin Quan | - |
dc.date.accessioned | 2019-09-18T08:35:14Z | - |
dc.date.available | 2019-09-18T08:35:14Z | - |
dc.date.issued | 2014 | - |
dc.identifier.citation | Science, 2014, v. 343, n. 6176, p. 1216-1220 | - |
dc.identifier.issn | 0036-8075 | - |
dc.identifier.uri | http://hdl.handle.net/10722/276981 | - |
dc.description.abstract | The use of ligands to tune the reactivity and selectivity of transition metal catalysts for C(sp3)-H bond functionalization is a central challenge in synthetic organic chemistry. Herein, we report a rare example of catalyst-controlled C(sp3)-H arylation using pyridine and quinoline derivatives: The former promotes exclusive monoarylation, whereas the latter activates the catalyst further to achieve diarylation. Successive application of these ligands enables the sequential diarylation of a methyl group in an alanine derivative with two different aryl iodides, affording a wide range of β-Ar-β-Ar?-α-amino acids with excellent levels of diastereoselectivity (diastereomeric ratio > 20:1). Both configurations of the β-chiral center can be accessed by choosing the order in which the aryl groups are installed. The use of a quinoline derivative as a ligand also enables C(sp3)-H olefination of a protected alanine. | - |
dc.language | eng | - |
dc.relation.ispartof | Science | - |
dc.title | Ligand-controlled C(sp3)-H arylation and olefination in synthesis of unnatural chiral α-amino acids | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1126/science.1249198 | - |
dc.identifier.pmid | 24626923 | - |
dc.identifier.scopus | eid_2-s2.0-84896050363 | - |
dc.identifier.volume | 343 | - |
dc.identifier.issue | 6176 | - |
dc.identifier.spage | 1216 | - |
dc.identifier.epage | 1220 | - |
dc.identifier.eissn | 1095-9203 | - |
dc.identifier.isi | WOS:000332728500029 | - |
dc.identifier.issnl | 0036-8075 | - |