| Autor: |
Yunliang Yu, Nazarii Sabat, Meriem Daghmoum, Zhenhao Zhang, Pascal Retailleau, Gilles Frison, Angela Marinetti, Xavier GUINCHARD |
| Rok vydání: |
2023 |
| DOI: |
10.26434/chemrxiv-2023-s8hq5 |
| Popis: |
The enantioselective tandem cycloisomerization / addition reactions of 2-alkynyl enones with 1- and 2-naphthols have been investigated using gold(I) catalysts featuring hybrid phosphine-phosphoric acid ligands, according to the Tethered Counteri-on-Directed Catalysis strategy. The reactions occur at low catalytic loading (0.2-1 mol%), without silver additives, and the naphthols act as both O- and C-nucleophiles, leading to the corresponding addition products in high yields and enantioselec-tivities. Monitoring of the reaction course highlights both conversion of O-addition into C-addition products and racemiza-tion processes that can affect the enantiomeric excess of the final products. Examples of solvent-dependent enantiodiver-gence, as well as further conversion of the C-addition products into highly enantioenriched heteropolycycles are shown. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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