A Serendipitous Synthesis of Bis-Heterocyclic Spiro 3(2H)-Furanones
| Autor: | Alfredo Picado, ShengJian Li, R. Karl Dieter |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Trifluoromethyl
010405 organic chemistry Organic Chemistry Nucleophilic acyl substitution Iminium 010402 general chemistry Ring (chemistry) 01 natural sciences Medicinal chemistry Enol 0104 chemical sciences chemistry.chemical_compound chemistry Reagent Organic chemistry Trifluoromethanesulfonate Carbanion |
| Zdroj: | The Journal of Organic Chemistry. 81:1391-1400 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.5b02350 |
| Popis: | (Z) Enol triflates 6, 11b-d, (E) enol triflate 11e, and phenol triflate 11a, derived from β-keto esters or 2-carboalkoxy phenols, respectively, react with N-Boc 2-lithiopyrrolidine (5a), N-Boc N-methylaminomethyllithium (5b), or 2-lithio-1,3-dithiane (14) to afford 3(2H)-furanones in modest to good yields (38-81%). Product and carbanion reagent studies suggest that the 3(2H)-furanone is formed in a cascade of reactions involving nucleophilic acyl substitution, enolate formation, trifluoromethyl transfer, iminium or sulfenium ion formation, and subsequent ring closure to form the 3(2H)-furanone. The use of 2-lithio-1,3-dithiane affords a cyclic α-keto-S,S,O-orthoester in which the functionality can be selectively manipulated for synthetic applications. |
| Databáze: | OpenAIRE |
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