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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Yu, Jin-quan Spangler, Jillian E. Li, Suhua Fu, Haiyan He, Jian Homs, Anna Laforteza, Brian N. Deng, Youqian |
| Description | Author Affiliation: He J ( The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.) |
| Abstract | The use of ligands to tune the reactivity and selectivity of transition metal catalysts for C(sp(3))-H bond functionalization is a central challenge in synthetic organic chemistry. Herein, we report a rare example of catalyst-controlled C(sp(3))-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 ß-Ar-ß-Ar'- -amino acids with excellent levels of diastereoselectivity (diastereomeric ratio > 20:1). Both configurations of the ß-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(sp(3))-H olefination of a protected alanine. |
| ISSN | 00368075 |
| e-ISSN | 10959203 |
| Journal | Science |
| Issue Number | 6176 |
| Volume Number | 343 |
| Language | English |
| Publisher | American Association for the Advancement of Science (United States) |
| Publisher Date | 2014-03-14 |
| Publisher Place | United States |
| Access Restriction | Open |
| Subject Keyword | Amino Acids Chemical Synthesis Palladium Chemistry Pyridines Quinolines Alanine Alkenes Catalysis Hydrogen Bonding Ligands Stereoisomerism Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't Multidisciplinary |
| Content Type | Text |
| Resource Type | Article |
| Subject | History and Philosophy of Science |
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