Remote C6-Enantioselective C–H Functionalization of 2,3-Disubstituted Indoles through the Dual H-Bonds and π–π Interaction Strategy Enabled by CPAs
| Autor: | Jun-Chen Kang, Shu-Yu Zhang, Si-Hua Hou, Fu-Xin Tan, Zhi-Gang Ma, Guo-Dong Zhu, Jia Zhou, Wei Jiang, Le Wang |
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| Rok vydání: | 2019 |
| Předmět: |
Indole test
Reaction conditions Interaction strategy Indoles 010405 organic chemistry Chemistry Organic Chemistry Enantioselective synthesis Hydrogen Bonding Stereoisomerism 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Catalysis 0104 chemical sciences Yield (chemistry) Electrophile Surface modification Phosphoric Acids Physical and Theoretical Chemistry |
| Zdroj: | Organic Letters. 21:8662-8666 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.9b03276 |
| Popis: | A versatile dual H-bonds and π-π interaction strategy that enables enantioselective remote C6-selective C-H functionalization of 2,3-disubstituted indoles was first reported. The N-H bond of indole was pivotal to achieve the C6 functionalization with excellent yield and enantioselectivity. Furthermore, this methodology leads to the efficient construction of numerous enantioenriched C6-functionalized indole products under mild reaction conditions employing different electrophiles. Preliminary cell proliferation investigations revealed that the synthesized chiral C6-substituted indole derivatives had potential anticancer activities. |
| Databáze: | OpenAIRE |
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