Bifunctional Aluminum Catalyst for CO2 Fixation: "Regioselective Ring Opening of Three-Membered Heterocyclic Compounds
发表时间：2019-03-09
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- 论文类型：
- 期刊论文
- 第一作者：
- Ren, Wei-Min
- 通讯作者：
- Ren, WM (reprint author), Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China.
- 合写作者：
- Liu, Ye,Lu, Xiao-Bing
- 发表时间：
- 2014-10-17
- 发表刊物：
- JOURNAL OF ORGANIC CHEMISTRY
- 收录刊物：
- SCIE、EI、PubMed、Scopus
- 文献类型：
- J
- 卷号：
- 79
- 期号：
- 20
- 页面范围：
- 9771-9777
- ISSN号：
- 0022-3263
- 摘要：
- Regioselective ring opening of three-membered heterocyclic compounds (epoxides or N-substituted aziridines) at various temperatures was observed in coupling reactions with CO2 by the use of an aluminum-salen catalyst in conjunction with intramolecular quaternary ammonium salts as cocatalysts, affording the corresponding five-membered cyclic products with complete configuration retention at the methine carbon. Notably, this bifunctional aluminum-based catalyst exhibited nearly 100% regioselectivity for the ring opening at the methylene C-O bond for various terminal epoxides. This was true for those bearing an electron-withdrawing group, such as styrene oxide or epichlorohydrin, thereby affording the synthesis of various enantiopure cyclic carbonates that have previously been obtained only rarely by other methods. An intramolecular cooperative catalysis is suggested to contribute to the high activity and excellent stereochemistry control observed. Surprisingly, the highly selective ring opening at the methine carbon of N-substituted aziridines was found in the coupling with CO2, predominantly giving 5-substituted oxazolininones with retention of configuration as a result of double inversion at the methine carbon.
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