Quinine-Based Trifunctional Organocatalyst for Tandem Aza-Henry Reaction-Cyclization: Asymmetric Synthesis of Spiroxindole-Pyrrolidine/Piperidines
| Autor: | Saumen Hajra, Bibekananda Jana |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Nitroaldol reaction
Tandem 010405 organic chemistry Chemistry Hydrogen bond Organic Chemistry Enantioselective synthesis 010402 general chemistry 01 natural sciences Biochemistry Pyrrolidine 0104 chemical sciences Catalysis Bifunctional catalyst chemistry.chemical_compound Organic chemistry Physical and Theoretical Chemistry Demethylation |
| Zdroj: | Organic Letters. 19:4778-4781 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.7b02150 |
| Popis: | A quinine-derived trifunctional sulphonamide catalyst has been developed for the effective asymmetric organocatalytic tandem aza-Henry reaction-cyclization of isatin-derived ketimines and nitroalkane-mesylates for the synthesis of spiro-pyrrolidine/piperidine-oxindoles. Demethylation of traditional bifunctional catalyst to incorporate an additional hydrogen bonding C6'-OH group plays the key role toward remarkable enantioselectivity. |
| Databáze: | OpenAIRE |
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