Periodical
Palladium-Catalyzed Enantioselective C(sp3)–H Arylation of 2-Propyl Azaaryls Enabled by an Amino Acid Ligand
| العنوان: | Palladium-Catalyzed Enantioselective C(sp3)–H Arylation of 2-Propyl Azaaryls Enabled by an Amino Acid Ligand |
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| المؤلفون: | Li, Hong-Liang, Yang, Deng-Feng, Jing, Hua-Qing, Antilla, Jon C., Kuninobu, Yoichiro |
| المصدر: | Organic Letters; February 2022, Vol. 24 Issue: 6 p1286-1291, 6p |
| مستخلص: | A palladium(II)-catalyzed enantioselective arylation of unbiased secondary C(sp3)–H bonds was developed. The enantioselectivity was controlled by the combination of a pyridyl or isoquinolinyl directing group and an amino acid, N-Boc-2-pentyl proline. A variety of 2-propyl azaaryls and biaryl iodides were employed to provide arylated products in moderate to good yields (up to 82%) with high enantioselectivities (up to 93:7 er). This reaction is a rare example of an amino-acid-enabled enantioselective acyclic methylene C(sp3)–H arylation. Furthermore, the reaction proceeded with high enantioselectivity even on a gram scale, and the product was transformed to a 5,6,7,8-tetrahydroisoquinoline bioactive molecule. Kinetic isotope effect (KIE) experiments indicated that C–H activation is the rate-determining step for the enantioselective C(sp3)–H arylation. |
| قاعدة البيانات: | Supplemental Index |
| تدمد: | 15237060 15237052 |
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| DOI: | 10.1021/acs.orglett.1c04215 |