Synthesis of Functionalized 3,4-Dihydropyrans via Rearrangement of the Products of a One-Pot Diastereoselective Assembly of Ketones and Acetylene

Synthesis of Functionalized 3,4-Dihydropyrans via Rearrangement of the Products of a One-Pot Diastereoselective Assembly of Ketones and Acetylene

The products of the one‐pot assembly of ketones and acetylene, 7‐methylene‐6,8‐dioxabicyclo[3.2.1]octanes, congeners of an insect pheromone frontalin, undergo an acid‐catalyzed rearrangement to diastereomerically pure 2‐acetyl‐3,4‐dihydropyrans in excellent yields. The synthesis is realizable in a o...

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Veröffentlicht in:European Journal of Organic Chemistry 2010-12, Vol.2010 (35), p.6727-6730
Hauptverfasser: Schmidt, Elena Yu, Trofimov, Boris A., Zorina, Nadezhda V., Mikhaleva, Albina I., Ushakov, Igor A., Skital'tseva, Elena V., Kazheva, Olga N., Alexandrov, Grigorii G., Dyachenko, Oleg A.
Format: Artikel
Sprache:eng
Schlagworte:
Dihydropyran synthesis
Heterocycles
Oxygen heterocycles
Synthetic methods
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Zusammenfassung:The products of the one‐pot assembly of ketones and acetylene, 7‐methylene‐6,8‐dioxabicyclo[3.2.1]octanes, congeners of an insect pheromone frontalin, undergo an acid‐catalyzed rearrangement to diastereomerically pure 2‐acetyl‐3,4‐dihydropyrans in excellent yields. The synthesis is realizable in a one‐pot manner procedure directly from ketones and acetylene. The products of the one‐pot assembly of ketones and acetylene, 7‐methylene‐6,8‐dioxabicyclo[3.2.1]octanes, congeners of an insect pheromone frontalin, undergo an acid‐catalyzed rearrangement to diastereomerically pure 2‐acetyl‐3,4‐dihydropyrans in excellent yields. The synthesis is realizable in a one‐pot manner procedure directly from ketones and acetylene.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201001229