Synthesis of Novel Hexahydroindoles from the Dearomatization of Indoline
| Autor: | Michal Sabat, William H. Myers, Jared A. Pienkos, W. Dean Harman, Brianna L. MacLeod, Katy B. Wilson |
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| Rok vydání: | 2016 |
| Předmět: |
Nucleophilic addition
010405 organic chemistry Chemistry Electrophilic addition Stereochemistry Organic Chemistry Synthon Protonation Alkylation 010402 general chemistry 01 natural sciences 0104 chemical sciences Stereocenter Inorganic Chemistry chemistry.chemical_compound Indoline Physical and Theoretical Chemistry Amination |
| Zdroj: | Organometallics. 35:370-387 |
| ISSN: | 1520-6041 0276-7333 |
| DOI: | 10.1021/acs.organomet.5b00959 |
| Popis: | The transiently stable indoline complex TpW(NO)(PMe3)(η2-N-ethyl-6,7-indoline) is shown to be a synthon for a broad range of novel hexahydroindoles. The tungsten dearomatizes the indoline, allowing for its sequential protonation, electrophilic addition (e.g., protonation, fluorination, hydroxylation, acylation), nucleophilic addition (e.g., amination, arylation, etheration, alkylation), and reduction, all with well-defined and predictable stereochemistry. The tungsten stereocenter directly governs the stereoselective formation of four adjacent asymmetric carbons originating from the aromatic ring of the indoline. |
| Databáze: | OpenAIRE |
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