Palladium-catalyzed intermolecular [4 + 2] formal cycloaddition with (Z)-3-iodo allylic nucleophiles and allenamides
| Autor: | Bing Ai, Fachao Yan, Pingping Zhao, Luyang Jiao, Hui Liu, Yunhui Dong, Qing Liu, Wenjing Liang, Shuzhi Yao, Hanbing Liang |
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| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Allylic rearrangement Double bond 010405 organic chemistry Organic Chemistry Regioselectivity 010402 general chemistry Metathesis 01 natural sciences Biochemistry Medicinal chemistry Cycloaddition 0104 chemical sciences Grubbs' catalyst chemistry.chemical_compound Nucleophile chemistry SN2 reaction Physical and Theoretical Chemistry |
| Zdroj: | Organicbiomolecular chemistry. 17(10) |
| ISSN: | 1477-0539 |
| Popis: | A highly chemo- and regioselective [4 + 2] formal cycloaddition of (Z)-3-iodo allylic nucleophiles and allenamides catalyzed by palladium is reported. The methodology proceeds under mild reaction conditions and is tolerant of alkyl and aryl functional groups. The SN2' substitution at the proximal C[double bond, length as m-dash]C bond performed against the Heck or SN2 pathway delivered a variety of 2-amino-dihydropyrans and 2-amino-tetrahydropiperidines in moderate to satisfactory yields. The [4 + 2] formal cycloaddition derivatives are convertible to interesting scaffolds 2,6,7,7a-tetrahydropyrano[2,3-b]pyrrole and 2,6,7,7a-tetrahydro-1H-pyrrolo[2,3-b]pyridine derivatives via ring-closing metathesis (RCM) with Grubbs catalyst II. |
| Databáze: | OpenAIRE |
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