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- Publisher Website: 10.1126/science.aal5175
- Scopus: eid_2-s2.0-85011397637
- PMID: 28154075
- WOS: WOS:000393183100039
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Article: Formation of α-chiral centers by asymmetric β-C(sp3)-H arylation, alkenylation, and alkynylation
Title | Formation of α-chiral centers by asymmetric β-C(sp3)-H arylation, alkenylation, and alkynylation |
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Authors | |
Issue Date | 2017 |
Citation | Science, 2017, v. 355, n. 6324, p. 499-503 How to Cite? |
Abstract | © 2017, American Association for the Advancement of Science. All rights reserved. The enzymatic β-C-H hydroxylation of the feedstock chemical isobutyric acid has enabled the asymmetric synthesis of a wide variety of polyketides. The analogous transition metal-catalyzed enantioselective β-C-H functionalization of isobutyric acid-derived substrates should provide a versatile method for constructing useful building blocks with enantioenriched α-chiral centers from this abundant C-4 skeleton. However, the desymmetrization of ubiquitous isopropyl moieties by organometallic catalysts has remained an unanswered challenge. Herein, we report the design of chiral mono-protected aminomethyl oxazoline ligands that enable desymmetrization of isopropyl groups via palladium insertion into the C(sp 3 )-H bonds of one of the prochiral methyl groups. We detail the enantioselective β-arylation, -alkenylation, and -alkynylation of isobutyric acid/2-aminoisobutyric acid derivatives, which may serve as a platform for the construction of α-chiral centers. |
Persistent Identifier | http://hdl.handle.net/10722/277058 |
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 | Wu, Qing Feng | - |
dc.contributor.author | Shen, Peng Xiang | - |
dc.contributor.author | He, Jian | - |
dc.contributor.author | Wang, Xiao Bing | - |
dc.contributor.author | Zhang, Forrest | - |
dc.contributor.author | Shao, Qian | - |
dc.contributor.author | Zhu, Ru Yi | - |
dc.contributor.author | Mapelli, Claudio | - |
dc.contributor.author | Qiao, Jennifer X. | - |
dc.contributor.author | Poss, Michael A. | - |
dc.contributor.author | Yu, Jin Quan | - |
dc.date.accessioned | 2019-09-18T08:35:29Z | - |
dc.date.available | 2019-09-18T08:35:29Z | - |
dc.date.issued | 2017 | - |
dc.identifier.citation | Science, 2017, v. 355, n. 6324, p. 499-503 | - |
dc.identifier.issn | 0036-8075 | - |
dc.identifier.uri | http://hdl.handle.net/10722/277058 | - |
dc.description.abstract | © 2017, American Association for the Advancement of Science. All rights reserved. The enzymatic β-C-H hydroxylation of the feedstock chemical isobutyric acid has enabled the asymmetric synthesis of a wide variety of polyketides. The analogous transition metal-catalyzed enantioselective β-C-H functionalization of isobutyric acid-derived substrates should provide a versatile method for constructing useful building blocks with enantioenriched α-chiral centers from this abundant C-4 skeleton. However, the desymmetrization of ubiquitous isopropyl moieties by organometallic catalysts has remained an unanswered challenge. Herein, we report the design of chiral mono-protected aminomethyl oxazoline ligands that enable desymmetrization of isopropyl groups via palladium insertion into the C(sp 3 )-H bonds of one of the prochiral methyl groups. We detail the enantioselective β-arylation, -alkenylation, and -alkynylation of isobutyric acid/2-aminoisobutyric acid derivatives, which may serve as a platform for the construction of α-chiral centers. | - |
dc.language | eng | - |
dc.relation.ispartof | Science | - |
dc.title | Formation of α-chiral centers by asymmetric β-C(sp3)-H arylation, alkenylation, and alkynylation | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1126/science.aal5175 | - |
dc.identifier.pmid | 28154075 | - |
dc.identifier.scopus | eid_2-s2.0-85011397637 | - |
dc.identifier.volume | 355 | - |
dc.identifier.issue | 6324 | - |
dc.identifier.spage | 499 | - |
dc.identifier.epage | 503 | - |
dc.identifier.eissn | 1095-9203 | - |
dc.identifier.isi | WOS:000393183100039 | - |
dc.identifier.issnl | 0036-8075 | - |