| Autor: |
Yu‐Qing Xiao, Miao‐Miao Li, Zheng‐Xin Zhou, Yu‐Jie Li, Meng‐Yue Cao, Xiao‐Peng Liu, Hai‐Hua Lu, Li Rao, Liang‐Qiu Lu, André M. Beauchemin, Wen‐Jing Xiao |
| Rok vydání: |
2022 |
| Předmět: |
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| Zdroj: |
Angewandte Chemie (International ed. in English). 62(3) |
| ISSN: |
1521-3773 |
| Popis: |
Ring-opening transformations of donor-acceptor (D-A) cyclopropanes enable the rapid assembly of complex molecules. However, the enantioselective formation of chiral quaternary stereocenters using substrates bearing two different acceptors remains a challenge. Herein, we describe the first palladium-catalyzed highly diastereo- and enantioselective (3+2) cycloaddition of vinyl cyclopropanes bearing two different electron-withdrawing groups, a subset of D-A cyclopropanes. The key to the success of this reaction is the remote stereoinduction through hydrogen bond from chiral ligands, which thereby addressed the aforementioned challenge. A variety of chiral five-membered heterocycles were produced in good yields and with high stereoselectivity (up to 99 % yields, 99 : 1 er and19 : 1 dr). In-depth mechanistic investigations, including control experiments and theoretical calculations, revealed the origin of the stereoselectivity and the importance of H-bonding in stereocontrol. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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