Palladium-Catalyzed Double Allylation of Sugar-Imines by Employing Tamaru–Kimura’s Protocol: Access to Unnatural Iminosugars
| Autor: | Batchu Venkateswara Rao, Kanakaraju Marumudi, Annavareddi Naresh, A. C. Kunwar |
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| Rok vydání: | 2017 |
| Předmět: |
010405 organic chemistry
Organic Chemistry chemistry.chemical_element Indolizidine 010402 general chemistry 01 natural sciences Biochemistry Pyrrolidine 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Cascade reaction Nucleophile Organic chemistry Piperidine Physical and Theoretical Chemistry Palladium |
| Zdroj: | Organic Letters. 19:1642-1645 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.7b00441 |
| Popis: | Conversion of vinyl pyranosylamine and vinyl furanosylamines to 2,6- and 2,5-disubstituted pyrrolidine and piperidine iminosugars, respectively, in one pot was developed using Kimura and Tamaru’s procedure, where a Pd salt in the presence of Et2Zn was used for the domino reaction. In this procedure, double allylation, which involves nucleophilic allylation–heterocyclization, took place to give desired nitrogen heterocycles. This strategy was further elaborated to synthesize some unnatural deoxycalystegines, hydroxylated pyrrolidines, piperidines, and indolizidine analogues. |
| Databáze: | OpenAIRE |
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