Catalytic enantioselective aza-Diels–Alder reactions of unactivated acyclic 1,3-dienes with aryl-, alkenyl-, and alkyl-substituted imines
| Autor: | Tomoyuki Otsuka, Shuuto Nantaku, Tohru Sekikaw, Yasuo Hatanaka, Yuhki Nishimura |
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| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Aryl Metals and Alloys Enantioselective synthesis General Chemistry Ion pairs 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Surfaces Coatings and Films Electronic Optical and Magnetic Materials Adduct chemistry.chemical_compound chemistry Materials Chemistry Ceramics and Composites Diels alder Organic chemistry Brønsted–Lowry acid–base theory Alkyl |
| Zdroj: | Chemical Communications. 53:8996-8999 |
| ISSN: | 1364-548X 1359-7345 |
| DOI: | 10.1039/c7cc03010j |
| Popis: | A catalytic enantioselective aza-Diels-Alder reaction of unactivated acyclic dienes with aryl-, alkenyl-, and alkyl-substituted imines is described. With 5-10 mol% loadings of a new Brønsted acid catalyst, the aza-Diels-Alder reaction of unactivated acyclic dienes proceeded to give the corresponding aza-Diels-Alder adducts in high yields (up to 98%) with excellent enantioselectivity (up to 98% ee). Preliminary DFT calculations suggest that the reaction proceeds through a chiral ion pair intermediate. |
| Databáze: | OpenAIRE |
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