Formation of Seven-Membered Carbocycles via 7-endo Mode Cyclization of Lithioheptatrienes
| Autor: | Kiyohiko Nakajima, Ken-ichiro Kanno, Tamotsu Takahashi, Eri Igarashi, Yuki Mizukami, Zhiyi Song |
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| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Chemistry Organic Chemistry Allyl halides 010402 general chemistry Highly selective Organolithium reagent 01 natural sciences Biochemistry Medicinal chemistry Coupling reaction 0104 chemical sciences chemistry.chemical_compound Organic chemistry Physical and Theoretical Chemistry |
| Zdroj: | Organic Letters. 18:6217-6219 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | The highly selective synthesis of triene derivatives was achieved by a zirconocene-mediated three-component coupling reaction, and the trienes were efficiently subjected to 7-endo mode cyclization. The reaction of unsymmetrical zirconacyclopentadienes prepared from two different alkynes with N-bromosuccinimide (NBS) followed by treatment with allyl halides in the presence of CuCl afforded the corresponding heptatrienes in good yields. When the trienes reacted with an organolithium reagent, 7-endo mode cyclization occurred smoothly to give the corresponding cycloheptadiene. |
| Databáze: | OpenAIRE |
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