Atropisomeric Chiral Diiododienes (Z,Z)-2,3-Di(1-iodoalkylidene)tetralins: Synthesis, Enantiomeric Resolution, and Application in Asymmetric Catalysis
| Autor: | Yuta Amano, Kiyohiko Nakajima, Naoko Takenaga, Hao Hu, Toshifumi Dohi, Tamotsu Takahashi, Masamichi Ogasawara, Yasuyuki Kita, Hirotaka Sasa, Hikaru Nakajima |
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| Rok vydání: | 2017 |
| Předmět: |
Resolution (mass spectrometry)
010405 organic chemistry Stereochemistry Organic Chemistry Enantioselective synthesis 010402 general chemistry Chiral stationary phase 01 natural sciences Biochemistry 0104 chemical sciences chemistry.chemical_compound chemistry Tetralin Physical and Theoretical Chemistry Enantiomer Chiral derivatizing agent |
| Zdroj: | Organic Letters. 19:4102-4105 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.7b01876 |
| Popis: | The C2-symmetric tetralin-fused 1,4-diiodo-1,3-butadiene derivatives, (Z,Z)-2,3-di(1-iodoalkylidene)tetralin 1a-c, are atropisomeric and can be resolved into the two persistent axially chiral enantiomers by HPLC on a chiral stationary phase. The enantiomerically pure compounds can serve as chiral organocatalysts for dearomatizing spirolactonization to show good performances in up to 73 % ee. |
| Databáze: | OpenAIRE |
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