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- Publisher Website: 10.1021/ja512690x
- Scopus: eid_2-s2.0-84924706379
- PMID: 25697780
- WOS: WOS:000351187200035
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Article: Ligand-enabled β-C-H arylation of α-amino acids using a simple and practical auxiliary
Title | Ligand-enabled β-C-H arylation of α-amino acids using a simple and practical auxiliary |
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Authors | |
Issue Date | 2015 |
Citation | Journal of the American Chemical Society, 2015, v. 137, n. 9, p. 3338-3351 How to Cite? |
Abstract | © 2015 American Chemical Society. Pd-catalyzed β-C-H functionalizations of carboxylic acid derivatives using an auxiliary as a directing group have been extensively explored in the past decade. In comparison to the most widely used auxiliaries in asymmetric synthesis, the simplicity and practicality of the auxiliaries developed for C-H activation remains to be improved. We previously developed a simple N-methoxyamide auxiliary to direct β-C-H activation, albeit this system was not compatible with carboxylic acids containing α-hydrogen atoms. Herein we report the development of a pyridine-type ligand that overcomes this limitation of the N-methoxyamide auxiliary, leading to a significant improvement of β-arylation of carboxylic acid derivatives, especially α-amino acids. The arylation using this practical auxiliary is applied to the gram-scale syntheses of unnatural amino acids, bioactive molecules, and chiral bis(oxazoline) ligands. |
Persistent Identifier | http://hdl.handle.net/10722/277022 |
ISSN | 2023 Impact Factor: 14.4 2023 SCImago Journal Rankings: 5.489 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Chen, Gang | - |
dc.contributor.author | Shigenari, Toshihiko | - |
dc.contributor.author | Jain, Pankaj | - |
dc.contributor.author | Zhang, Zhipeng | - |
dc.contributor.author | Jin, Zhong | - |
dc.contributor.author | He, Jian | - |
dc.contributor.author | Li, Suhua | - |
dc.contributor.author | Mapelli, Claudio | - |
dc.contributor.author | Miller, Michael M. | - |
dc.contributor.author | Poss, Michael A. | - |
dc.contributor.author | Scola, Paul M. | - |
dc.contributor.author | Yeung, Kap Sun | - |
dc.contributor.author | Yu, Jin Quan | - |
dc.date.accessioned | 2019-09-18T08:35:22Z | - |
dc.date.available | 2019-09-18T08:35:22Z | - |
dc.date.issued | 2015 | - |
dc.identifier.citation | Journal of the American Chemical Society, 2015, v. 137, n. 9, p. 3338-3351 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10722/277022 | - |
dc.description.abstract | © 2015 American Chemical Society. Pd-catalyzed β-C-H functionalizations of carboxylic acid derivatives using an auxiliary as a directing group have been extensively explored in the past decade. In comparison to the most widely used auxiliaries in asymmetric synthesis, the simplicity and practicality of the auxiliaries developed for C-H activation remains to be improved. We previously developed a simple N-methoxyamide auxiliary to direct β-C-H activation, albeit this system was not compatible with carboxylic acids containing α-hydrogen atoms. Herein we report the development of a pyridine-type ligand that overcomes this limitation of the N-methoxyamide auxiliary, leading to a significant improvement of β-arylation of carboxylic acid derivatives, especially α-amino acids. The arylation using this practical auxiliary is applied to the gram-scale syntheses of unnatural amino acids, bioactive molecules, and chiral bis(oxazoline) ligands. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of the American Chemical Society | - |
dc.title | Ligand-enabled β-C-H arylation of α-amino acids using a simple and practical auxiliary | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/ja512690x | - |
dc.identifier.pmid | 25697780 | - |
dc.identifier.scopus | eid_2-s2.0-84924706379 | - |
dc.identifier.volume | 137 | - |
dc.identifier.issue | 9 | - |
dc.identifier.spage | 3338 | - |
dc.identifier.epage | 3351 | - |
dc.identifier.eissn | 1520-5126 | - |
dc.identifier.isi | WOS:000351187200035 | - |
dc.identifier.issnl | 0002-7863 | - |